4-Bromobenzenesulfonamide → 4-[2-(4-Chlorophenyl)phenyl]benzenesulfonamide

HRID 1839924Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2B(O)O)=[CH:4][CH:3]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 696964-Bromobenzenesulfonamide

HCID 234509984'-Chlorobiphenyl-2-boronic acid

Product 1

HCID 105453544-[2-(4-Chlorophenyl)phenyl]benzenesulfonamideYield 67%

Procedure

Following the general procedure outlined in Synthetic Scheme IX, 1.6 g (6.9 mmol) of 2-(4-chlorophenyl)phenylboronic acid (Step 2) was reacted with 1.8 g (7.6 mmol) of 4-bromobenzenesulfonamide. Purification by silica gel chromatography (Waters LC-2000) with ethyl acetate/hexane (3:7) and subsequent recrystallization from ethyl acetate/hexane gave 1.59 g (67%) of 4-(2-(4-chlorophenyl)phenyl]benzenesulfonamide as a colorless solid: mp 206.2-207.0° C.; NMR (CDCl3) δ 4.77 (s, 2H), 7.04 (d, J=9 Hz, 2H), 7.16-7.31 (m, 4H), 7.36-7.51 (m, 4H), 7.80 (d, J=9 Hz, 2H). MS (EI): m/e (rel intensity) 343 (100), 308 (13), 262 (21), 228 (82); HRMS Calc'd for C18H14ClNO2S: 343.0434. Found: 343.0434. Anal. Calc'd for C18 H14ClNO2S: C, 62.88; H, 4.10; N, 4.07. Found: C, 62.66; H, 4.36; N, 4.09.

Workup

customPurification by silica gel chromatography (Waters LC-2000)
customwith ethyl acetate/hexane (3:7) and subsequent recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record: ord-9ab74484df6c40b5a58124655047657c
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677488B2

Reaction notes

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