Supplementary Material (ESI) for Green Chemistry This journal is The Royal Society of Chemistry Supporting Information
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1 Supporting Information Eco-friendly and versatile brominating reagent prepared from liquid bromine precursor Subbarayappa Adimurthy, 1 Gadde Ramachandraiah, 1,*, Ashutosh V. Bedekar, 1 Sudip Ghosh, 2 Brindaban C. Ranu 2,* and Pushpito K. Ghosh 1,* 1 Central Salt and Marine Chemicals Research Institute, Gijubhai Badheka Marg, Bhavnagar , Gujarat, India. 2 Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata , India Address: pkghosh@csmcri.org/ grama@csmcri.org/ ocbcr@iacs.res.in Generation of BrOH from 2:1 mole ratio of Br /BrO 3. Absorption spectra of BrOH were recorded on UV-Vis-NIR CARY-500 spectrophotometer. The absorption spectra vs. time of the 2:1 NaBr:NaBrO 3 (total Br = M) reagent in aqueous solution containing N HCl is shown in Figure 1 below. The spectra were recorded at 25 C in 1 cm quartz cell at 5 min intervals immediately after sample preparation with absorbance at 260 nm increasing with time. 1 2 Absorbance Wavelength, nm Figure 1 Reaction Calorimetric study of the BPA to TBBP-A process. This was carried out in the reaction calorimeter described in the Experimental Section. 15 g (65.8 mmol) of bisphenol A, 75 ml of dichloromethane and 150 ml of an aqueous solution containing S1
2 stoichiometric amount of the brominating reagent were taken in the vessel. Stoichiometric amount of 12 N HCl was added slowly through a dropping funnel maintaining the temperature of the reaction mixture between o C. After addition of HCl, stirring was continued for 30 min and the reaction mixture was drained off. The overall heat evolved 71.9 kj/kg of reaction mass, which yields an adiabatic temperature rise of 18 o C. The total heat evolved was nearly the same as the heat evolved till the completion of addition of HCl indicating that the reaction is fast and goes to completion as HCl addition is over. Analytical data (Table 1) Monobromophenol (entry 1, table 1). Crude mixture analyzed by GC on SC-30 column with temperature ramp from 120 o C to 200 o 2 o C/min (please see GC below). Peaks at min and correspond to 2-bromophenol and 4-bromophenol, respectively, in the ratio of 19:81. 2,4,6-Tribromophenol (entry 2, table 1). 1 H-NMR (CDCl MHz): (δ) 7.7 (2H, s); 5.89 (1H, broad s). IR: ν max (KBr): 3407, 3070, 2358, 1552, 1454, 1379, 1317, 1263, 1228, 1158, 856, 736, 667, 552 cm -1. CHN: Found C, 22.04%; H, 0.84%; Calcd. C, 21.75%; H, 0.90%. Melting point: Observed C; Reported C. 2,4,4,6-tetrabromo-2,5-cyclohexadienone (entry 3, table 1). 1 H-NMR (CDCl MHz) (δ) 7.78 (2H, s). IR: ν max (KBr) 3051, 1680, 1582, 1454, 1310, 900, 702, 663, 634 cm -1. CHN: Found C, 17.16%; H, 0.24%; Calcd. C,17.56%; H, 0.49%. Melting point: Observed C. (Reported C) S2
3 4,6-Dibromo-2-chlorophenol (entry 4, table 1). 1 H-NMR (CDCl MHz) (δ) 7.56 (1H, s); 7.46 (1H, s); 5.91 (1H, broad s). IR: ν max (KBr) 3501, 3081, 1707, 1580, 1477, 1399, 1324, 1277, 1184, 1084, 814, 765, 710, 626, 553 cm -1. CHN : Found C, 25.01%; H, 0.74%; Calcd. C, 25.17%; H, 1.04%. 2,6-Dibromo-4-chlorophenol (entry 5, table 1). 1 H-NMR (CDCl MHz) (δ) 7.45 (2H, s); 5.86 (1H, broad s). IR: ν max (KBr) 3410, 3078, 1555, 1458, 1385, 1319, 1265, 1216, 1158, 855, 740, 701 cm -1. CHN : Found C, 26.70%; H, 1.11%; Calcd. C, 25.17%; H, 1.04%. 4, 6-Dibromo-2-nitrophenol (entry 6, table 1). 1 H-NMR (CDCl MHz) (δ) 8.41 (1H, s); 8.24 (1H, s); (1H, s). IR: ν max (KBr) 3551, 3473, 3414, 3163, 3074, 1599, 1531, 1450, 1393, 1327, 1242, 1151, 1111, 885, 761, 736, 674, 607, 554 cm -1. CHN: Found C, 24.85%; H, 0.86 %; N, 4.54 %; Calcd. C, 24.24%; H, 1.01%; N, 4.71 %. Melting point: Observed C (Reported 118 C). 2,6-Dibromo-4-nitrophenol (entry 7, table 1). 1 H-NMR (CDCl MHz) (δ) (1H, s); 7.21 (1H, s); 5.54 (1H, broad s); 2.27 (3H, s). IR: ν max (KBr) 3499, 3404, 3079, 1588, 1565, 1465, 1396, 1316, 1222, 1136, 997, 855, 677, 555 cm -1. CHN: Found C, 24.93%; H, 0.76 %; N, 4.63%; Calcd. C, 24.24%; H, 1.01%; N, 4.71 %. Melting point: Observed C (decomposed) (Reported 145 C). 2,6-Dibromo-4-methyl phenol (entry 8, table 1). 1 H-NMR (CDCl MHz) (δ) 7.33 (2H, s); 5.84 (1H, broad s); 2.25 (3H, s). IR: ν max (KBr) 3632, 3497, 2923, 1681, 1560, 1476, 1319, 1274, 1234, 1161, 852, 776, 737, 704, 559 cm -1. CHN: Found C, S3
4 32.34%; H, 3.12 %; Calcd. C, 31.57; H, 2.25%. Melting point: Observed C, (Reported 50 C). 4,6-Dibromo-2-methyl phenol (entry 9, table 1). 1 H-NMR (CDCl MHz) (δ) (1H, s); 7.21 (1H, s); 5.54 (1H, broad s); 2.27 (3H, s). IR: ν max (KBr) 3499, 3404, 3079, 1588, 1565, 1465, 1396, 1316, 1222, 1136, 997, 855, 677, 555 cm -1. CHN: Found C, 32.08%; H, 2.10%; Calcd. C, 31.57; H, 2.25%. Melting point: Observed C. 4-Bromo-2,6-dimethyl phenol (entry 10, table 1). 1 H-NMR (CDCl MHz) (δ) 7.25 (2H, s); 4.61 (1H, broad s); 2.21 (6H, s). IR: ν max (KBr) 3372, 2977, 2946, 2916, 1609, 1474, 1329, 1188, 1029, 939, 853, 716 cm -1. CHN : Found C, 48.23%; H, 3.98%; Calcd. C, 47.76%; H, 4.47%. Melting point: Observed C (Reported. 76 C). 2, 6 Dibromo-4-Bu t phenol (entry 11, table 1). 1 H-NMR (CDCl MHz) (δ) 7.42 (2H, s); 5.95 (1H,broad s) 1.24 (9H, s). IR: ν max (KBr) 3634, 3506, 2963, 2908, 2869, 1725, 1558, 1478, 1393, 1364, 1321, 1243, 1205, 1162, 1044, 870, 821, 737, 710 cm -1. CHN: Found C, 40.09%; H, 4.45%; Calcd. C, 38.96%; H, 3.89%. 1-Bromo-2-naphthol (entry 12, table 1). 1 H-NMR (CDCl MHz) (δ) (1H,d J= 8.0); 7.79 (2H, d J=8.0); 7.59 (1H, t J= 6.0); 7.42 (1H, t J= 8.0); 7.27 (1H, t J=6.0); 5.21 (1H, broad s). IR: ν max (KBr) 3275, 3056, 1629, 1601, 1500, 1432, 1347, 1301, 1234, 984, 928, 810, 744, 517 cm -1. CHN: Found C, 54.09%; H, 2.65%; Calcd. C, 53.80%; H, 3.13%. Melting point: Observed C (Reported 80 C). Tetrabromobisphenol-A (entry 13, table 1). 1 H-NMR (CDCl MHz) (δ) 7.25 (4H, s); 5.79 (2H, s); 1.58 (6H, s). IR: ν max (KBr) 3514, 3479, 2987, 1554, 1472, 1396, 1363, 1321, 1273, 1239, 1160, 1129, 868, 778, 731, 707, 615 cm -1. CHN: Found C: S4
5 32.80%; H, 2.25; Calcd. C, 33.08%; H, 2.20%. Melting point: Observed C (Reported C). Analytical data (Table 2) 2,4,6-Tribromoaniline (entry 1, table 2). 1 H-NMR (CDCl MHz) (δ) 7.5 (2H, s); 4.55 (2H, broad s). IR: ν max (KBr) 3414, 3290, 1615, 1562, 1541,1454, 1382, 1066, 859, 732, 706,547 cm -1. CHN: Found C, 22.10%; H, 1.04%; N, 4.14%; Calcd. C, 21.81%; H, 1.21%; N, 4.24%. Melting point: Observed C (Reported C). 2, 6-Dibromo-4-nitroaniline (entry 2, table 2). 1 H-NMR (CDCl MHz) (δ) 8.34 (2H, s); 6.64 (2H, broad s). IR: ν max (KBr) 3480, 3372, 1604, 1501, 1472, 1319, 1299, 1269, 1126, 899, 731, 693 cm -1. CHN: Found C, 24.82%; H, 0.59%; N, 9.39%; Calcd.. C, 24.32%; H, 1.35%; N, 9.45%. Melting point: Observed C (Reported C). 4, 6-Dibromo-2-nitroaniline (entry 3, table 2). 1 H-NMR (CDCl MHz) (δ) 8.29 (1H, s); 7.81 (1H, s); 6.64 (2H, broad s). IR: ν max (KBr) 3465, 3352, 1623, 1542, 1495, 1444, 1344, 1317, 1254, 1118, 1095, 873, 760, 689 cm -1. CHN: Found C, %; H, 0.60%; N, 9.01 %; Calcd. C, %; H, 1.35 %; N, 9.46 %; Melting point: Observed C (Reported 128 C). 2,6-Dibromo-4-methylaniline (entry 4, table 2). 1 H-NMR (CDCl MHz) (δ) 7.2 (2H, s); 4.38 (2H, broad s); 2.07 (3H, s). IR: ν max (KBr) 3422, 3306, 2914, 1618, 1581, 1477, 1285, 1212, 1058, 853, 733, 706, 637, 557 cm -1. CHN: Found C, 32.19%; H, S5
6 2.18%; N, 5.18%; Calcd. C, 31.69%, H, 2.64%; N, 5.28%. Melting point: Observer C (Reported 75 C). 4-Bromo N, N-dimethylaniline (entry 5, table 2). 1 H-NMR (CDCl MHz) (δ) 7.31 (2H, d J= 8.0); 6.6 (2H, d J= 8.0 ); 2.91 (6H, s). IR: ν max (KBr) 3550, 3474, 3415, 2880, 2805, 1592, 1501, 1445, 1354, 1223, 1190, 1165, 1062, 944, 805, 750, 579, 505 cm -1. CHN: Found C, 47.22%; H, 4.33%; N, 6.74%; Calcd. C, 48.00%; H, 5.00%; N, 7.00%. Melting point: Observed C (Reported 55 C). Analytical data (Table 3) 4-Bromoanisole (entry 1, table 3). 1 H-NMR-(CDCl MHz) (δ) (2H, d J= 8.0); (2H, d J=8.0 ); 3.83 (3H, s). IR: ν max (Nujal Mull ) 3071, 3005, 2959, 2937, 2837, 2538, 2279, 2036, 1871, 1580, 1487, 1380, 1288, 1247, 1179, 1032, 871, 822, 750, 680, 621, 600, 507 cm -1. CHN: Found C, 44.29%; H, 3.17%; Calcd. C, 44.92%; H, ,5-Dibromo-1,4-dimethoxy benzene (entry 2, table 3). 1 H-NMR (CDCl 3 -TMS) (δ) 7.10 (2H, s); 3.85 (6H, s). IR: ν max (KBr) 3494, 3099, 2969, 2944, 1699, 1667, 1494, 1436, 1358, 1275, 1212, 1185, 1065, 1021, 859, 759 cm -1. [Fig 5.17(B)]. CHN: Found C, 33.16%; H, 2.00%; Calcd. C,32.43%, H, 2.70%. Melting point: Observed C (Reported 147 C). 4-Bromoacetanilide (entry 3, table 3) 1 H-NMR (CDCl MHz) (δ) 7.44 (4H, m); 2.04 (3H, s), 1.66 (1H, s); IR: ν max (KBr) 3557, 3477, 3294, 3259, 3185, 3113, 1671, 1604, 1535, 1487, 1392, 1369, 1312, 1257, 1170, 1005, 822, 743, 690, 504 cm -1. CHN: S6
7 Found C, 44.89%, H, 3.36%; N, 6.5%; Calcd. C, 44.85%; H, 3.77%; N, 6.54%. Melting point: C (Reported C). Bromobenzene (entry 4, table 3) 1 H-NMR (CDCl MHz) (δ) 7.46 (2H, d J= 8.0); 7.19 (3H, d J= 8.0). IR: ν max (Neat) 3065, 1577, 1474, 1442, 1068, 1019, 999, 735, 682, 673 cm -1. CHN: Found C, 45.66%; H, 3.22%; Calcd. C, 45.86%, H, 3.18%. Boiling point: Observed C (Reported 156 C ). 1-Bromonaphthalene (entry 5, table 3) 1 H-NMR (CDCl MHz) (δ) 8.21 (1H, d J= 8.0); (3H, d J= 6.0); ( 2H, m) (1H, t J= 8.0). IR: ν max (Neat) 3054, 1591, 1561, 1501, 1378, 1253, 1199, 1161, 1135, 1021, 955, 790, 764, 650 cm -1. CHN: Found C,55.01%; H, 3.33%; Calcd. C, 57.97%; H: 3.38%. Analytical Data (Table 4) 2-Bromo-malonic acid diethyl ester (entry 1, Table 4). Yellowish oil; IR (neat): 1715cm -1 ; 1 H NMR (CDCl 3, 300 MHz): δ 1.32 (t, J = 7.2Hz, 3H), 4.30 (q, J = 7.2Hz, 2H), 4.85 (s, 1H); 13 CNMR (CDCl 3, 75 MHz) δ13.8 (2C), 55.4, 63.1 (2C), (2C) 2-Bromo-malonic acid dimethyl ester (entry 2, Table 4). Yellow oil; IR (neat):1722cm - 1; 1 H NMR (CDCl 3, 300 MHz): δ 3.85 (s, 6H), 4.87 (s,1h); 13 CNMR (CDCl 3, 75 MHz): δ 41.5, 53.9 (2C), (2C) 2-Bromo-3-oxo-butyric acid ethyl ester (entry 3, Table 4). Yellow oil; IR (neat) 1728cm- 1 ; 1 HNMR (CDCl 3, 300 MHz): δ 1.34 (t, J = 7.2 Hz, 3H), 2.44 (s, 3H), 4.29 (q, J = 7.2 Hz, 2H), 4.77 (s, 1H); 13 CNMR (CDCl 3, 75 MHz): δ 13.8, 26.3, 49.0, 63.1, 165.0, S7
8 2-Bromo-1,3-diphenyl-propane-1,3-dione(entry 4, Table 4). White solid; mp C ; IR (KBr):1672, 1693 cm- 1 ; 1 H NMR (CDCl 3, 300 MHz): δ 6.61 (s,1h), (m, 4H), (m, 2H), (m, 4H); 13 C NMR (CDCl 3, 75 MHz): δ 52.4,128.8 (4C), (4C), (2C), (2C),188.8 (2C) 2-Bromo-1-phenyl-butane-1,3-dione(entry 5, Table 4). Red oil; IR (neat): 1679, 1716, 1739cm -1 ; 1 HNMR (CDCl 3, 300 MHz): δ 2.44 (s, 3H), 5.66 (s, 1H), (m, 2H), (m, 1H), (m, 2H); 13 CNMR (CDCl 3, 75 MHz): δ 27.1, 52.9, (2C), (2C), 133.6, 134.4, 189.9, Bromo-2-oxo-cyclopentanecarboxylic acid ethyl ester (entry 7, Table 4). Brownish oil; ν max (neat)/cm , 1759; δ H /CDCl (t, J = 7.2 Hz, 3H), (m, 2H), (m, 3H), (m, 1H), 4.29 (q, J = 7.2 Hz, 2H); δ C /CDCl , 19.3, 35.2, 38.6, 54.6, 63.0, 166.7, (Found: C, 40.57, H, C 8 H 11 O 3 Br requires C, 40.87; 4.72 %). 1-Bromo-3-methyl-2-oxo-cyclohexanecarboxylic acid methyl ester (entry 8, Table 4). Yellow oil; ν max (neat)/cm , 1755; δ H /CDCl (d, J = 6.3 Hz, 3H), (m,2h), (m, 1H), (m, 2H) (m, 1H) (m, 1H), 3.78 (s, 3H); δ C /CDCl , 24.2, 35.7, 42.1, 44.2, 53.5, 68.2, 168.2, (Found: C, 43.19; H, 5.11.C 9 H 13 O 3 Br requires C, 43.39; H, 5.26%). Analytical data (Table 5) 1-Bromo-2-hexanol (entry 1, table 5) 1 H-NMR - (CDCl MHz)- (δ) (3H, t J=6); (6H, m); 2.16 (1H, br s); (2H, m); 3.77 (1H, m). IR: S8
9 ν max (Neat) 3393, 2958, 2932, 2862, 1463, 1423, 1379,1254, 1221, 1125, 1032, 903, 833, 789, 730, 663 cm -1. CHN: Found C, 38.39%; H, 7.34%; Calcd. C, 39.78%; H, 7.18 %. 1-Bromo-2-octanol (entry 2, table 5) 1 H-NMR- (CDCl MHz)- (δ) (3H, t J= 4); (10H, m); 1.99 (1H, s); (2H, m); (1H, m). IR: ν max (Neat) 3393, 2928, 2857, 1463, 1423, 1378, 1223, 1127, 1036, 663 cm - 1.CHN: Found C, 43.89%; H, 6.48%; Calcd. C, 45.93%; H, 8.13%. 2-Bromocyclohexanol (entry 3, table 5) 1 H-NMR- (CDCl MHz)- (δ) (3H, m); (3H, m); (1H, m); (1H, m); 2.57 (1H, s); (1H, m); (1H, m). IR: ν max (Neat) 3400, 2938, 2861, 1726, 1449, 1360, 1253, 1186, 1073, , 690 cm -1. CHN: Found C, 40.06%; H, 6.19%; Calcd. C, 40.22%; H, 6.15%. 2-Bromo-1-phenylethanol (entry 4, table 5) 1 H-NMR (CDCl MHz)- (δ) 2.53 (1H, s); (2H, m); (1H, dd J= 4 & 4); (5H, m). IR: ν max (Neat) 3403, 3063, 3031, 2962, 2893, 1956, 1887, 1813, 1680, 1493, 1452, 1420, 1256, 1217, 1198, 1118, 1061, 1028, 990, 917, 870, 813,762, 701, 666, 592 cm -1. CHN: Found C, 48.05%; H, 4.75%; Calcd. C, 47.76%; H, 4.47%. 2-Bromo-1-[4-methylphenyl] ethanol (entry 5, Table 5): 1 H-NMR- (CDCl MHz)- (δ) 2.63 (3H, s); (2H, m); (1H, dd J= 4 & 4); (5H, m). IR: ν max (Neat) 3400, 3024, 2960, 2922, 1613, 1514, 1421, 1379,1312, 1217, 1198, 1067, 1021, 993, 818, 765, 722, 643 cm -1. CHN: Found C, 47.68%; H, 4.47%; Calcd. C, 50.23%; H, 5.11%. S9
10 S10
11 Gas chromatogram (entry 1, Table 1) p/o bromophenol (81:19) S11
12 1 H-NMR (entry 2, Table 1) Ref 2. S12
13 DSC (entry 2, Table 1) S13
14 1 H-NMR (entry 3, Table 1) S14
15 1 H-NMR (entry 4, Table 1) S15
16 1 H-NMR (entry 5, Table 1) S16
17 1 H-NMR (entry 6, Table 1) S17
18 1 H-NMR (entry 7, Table 1) Ref 2 p 262. S18
19 1 H-NMR (entry 8, Table 1) Ref 2 p 290. S19
20 1 H-NMR (entry 9, Table 1) S20
21 1 H-NMR (entry 10, Table 1) Ref 2 p 289. S21
22 1 H-NMR (entry 11, Table 1) S22
23 1 H-NMR (entry 12, Table 1) Ref 2 p 309. S23
24 1 H-NMR (entry 13, Table 1) Ref 2 p 323. S24
25 HPLC (entry 13, Table 1) S25
26 DSC (entry 13, Table 1) (Tetrabromobisphenol-A) S26
27 1 H-NMR (entry 1, Table 2) S27
28 HPLC (entry 1, Table 2) S28
29 DSC (entry 1, Table 2) (Tribromoaniline) S29
30 1 H-NMR (entry 2, Table 2) Ref 2 p 765. S30
31 1 H-NMR (entry 3, Table 2) Ref 2 p 765. S31
32 1 H-NMR (entry 4, Table 2) Ref 2 p 525. S32
33 1 H-NMR (entry 5, Table 2) Ref 2 p 482. S33
34 1 H-NMR (entry 1, Table 3) Ref 2 p 187. S34
35 1 H-NMR (entry 3, Table 3) S35
36 1 H-NMR (entry 4, Table 3) Ref 2 p 61. S36
37 HPLC (entry 4, Table 3) S37
38 1 H-NMR (entry 5, Table 3) Ref 2 p 167. S38
39 1 H-NMR N-Bromosuccinimide (NBS) S39
40 (ENTRY-1, Table 4) S40
41 (ENTRY-2, Table 4) S41
42 (ENTRY-3, Table 4) S42
43 (ENTRY-4, Table 4) S43
44 (ENTRY-5, Table 4) S44
45 (ENTRY-7, Table 4) S45
46 (ENTRY-8, Table 4) S46
47 1 H-NMR (entry 1, Table 5) Ref 3a S47
48 1 H-NMR (entry 2, Table 5); Ref 3a S48
49 1 H-NMR (entry 3, Table 5) Ref 3a S49
50 1 H-NMR (entry 4, Table 5) Ref 3b. S50
51 1 H-NMR (entry 5, Table 5) S51
52 References 1 a) Kumar, K.; Margerum, D. W. Inorg. Chem. 1987, 26, b) Beckwith, R.C.; Margerrum, D. W. Inorg. Chem. 1997, 36, Pauchert, C. J.; Behnke, J. The Aldrich Library of 13 C and 1 H FT NMR Spectra Edition I, vol II, 1993, p a) Masuda, H. ; Takase, K. ; Nishio, M. ;Hasegawa, A. ; Nishiyama, Y. and Ishii, Y. J. Org. Chem. 1994, 59, b) Sharghi, H.; Niknam, K. and Pooyan, M. Tetrahedron 2001, 57,6057. S52
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