Bromobenzene → 4-Chlorobiphenyl

HRID 412809Notes

Reaction equation

HRID 412809 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acid

Product 1

HCID 163234-ChlorobiphenylYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bromobenzene (80 mg, 0.51 mmol) reacted with 4-chlorophenylboronic acid (103 mg, 0.66 mmol) using 0.5/1.0 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and K3PO4 (318 mg, 1.50 mmol) in toluene at 100° C. to give the title compound (75 mg, 78%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 7.41-7.62 (m, 9H). 13C{1H}-NMR (100 MHz, CDCl3): δ 139.95, 139.62, 133.33, 128.88, 128.86, 128.36, 127.56, 126.96. GC/MS(EI): m/z 188 (M+), 152

Workup

  1. customat 100° C.

Sources & evidence

ORD record
ord-a4d4f2d345c7475eb95e4a97fc0d2c86
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

Loading…