1,2-Dibromobenzene → 2-Bromo-4'-chloro-1,1'-biphenyl

HRID 1839923Notes

Reaction equation

HRID 1839923 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[Cl:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1>>[Br:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:13]1[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 114141,2-DibromobenzeneHCID 742994-Chlorophenylboronic acid

Product 1

HCID 129394052-Bromo-4'-chloro-1,1'-biphenylYield 86.4%

Procedure

Following the general procedure outlined in Synthetic Scheme III, 9.0 g (38 mmol) of 1,2-dibromobenzene was reacted with 3.0 g (19 mmol) of 4-chlorophenylboronic acid (Lancaster). Purification by silica gel chromatography (Waters Prep-500A) with hexane gave 4.39 g (84%) of 1-bromo-2-(4-chlorophenyl)benzene as a colorless oil: NMR (CDCl3) δ 7.18-7.26 (m, 1H), 7.28-7.44 (m, 6H), 7.68 (dd, J=1.5, 8 Hz, 1H).

Workup

  1. customPurification by silica gel chromatography (Waters Prep-500A) with hexane

Sources & evidence

ORD record
ord-1e43ec86a21e4692859536195021011e
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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