1-Bromo-2-chlorobenzene → 2-Chlorobiphenyl

HRID 412822

Reaction equation

HRID 412822 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8].[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F-].[K+]>C1COCC1>[Cl:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 127541-Bromo-2-chlorobenzeneHCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

Product 1

HCID 2492662-ChlorobiphenylYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromochlorobenzene (96 mg, 0.50 mmol) reacted with phenylboronic acid (79 mg, 0.65 mmol) using 1/2 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.50 mmol) in THF at room temperature to give the title compound (88 mg, 93%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 7.40-7.19 (m, 9H). 13C{1H}-NMR (100 MHz, CDCl3): δ 140.45, 139.33, 132.43, 131.32, 129.88, 129.39, 128.47, 127.99, 127.55, 126.77. GC/MS(EI):188 (M+), 190, 152, 76.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-254a2f7d832244deb599c719778a3d8d
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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