4-Bromobenzenesulfonamide → HCID 10782440, compound

HRID 1839922Notes

Reaction equation

[F: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>>[F: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 22610240HCID 22610240, compound

Product 1

HCID 10782440HCID 10782440, compoundYield 46%

Procedure

Following the general procedure outlined in Synthetic Scheme IX, 1.5 g (6.9 mmol) of 2-(4-fluorophenyl)phenylboronic acid (Step 1) was reacted with 2.5 g (10.4 mol) of 4-bromobenzenesulfonamide (Lancaster). Purification by silica gel chromatography (Waters LC-2000) with ethyl acetate/hexane (3:7) and subsequent recrystallization from ethyl acetate/hexane gave 1.04 g (46%) of 4-[2-(4-fluorophenyl)phenyl]benzenesulfonamide as a colorless solid: mp 187.3-188.2° C.; NMR (CDCl3) δ 4.83 (s, 2H), 6.92 (t, J=9 Hz, 2H), 7.02-7.11 (m, 2H), 7.27 (d, J=9 Hz, 2H), 7.36-7.50 (m, 4H), 7.78 (d, J=8 Hz, 2H) MS (EI): m/e (rel intensity) 327 (75) 245 (100); HRMS Calc'd for C18H14FNO2S: 327.0729. Found: 327.0743. Anal. Calc'd for C18H14FNO2S: C, 66.04; H, 4.31; N, 4.28. Found: C, 65.86; H, 4.51; N, 4.34.

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-3b77e653b73449889ed781e9cca3b18d
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677488B2

Reaction notes

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