4-Bromobenzaldehyde → 4'-Chloro[1,1'-biphenyl]-4-carbaldehyde

HRID 412803

Reaction equation

HRID 412803 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[F-].[K+]>C1COCC1>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 707414-BromobenzaldehydeHCID 742994-Chlorophenylboronic acidHCID 522689Potassium Fluoride

Product 1

HCID 5925704'-Chloro[1,1'-biphenyl]-4-carbaldehydeYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromobenzaldehyde (95 mg, 0.51 mmol) reacted with 4-chlorophenylboronic acid (101 mg, 0.65 mmol) using 0.5/1.0 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.55 mmol) in THF solvent at room temperature to give the title compound (110 mg, 99%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 10.07 (s, 1H, —CHO), 7.96 (d, 2H, J=7.04 Hz), 7.73 (d, 2H, J=7.04 Hz), 7.58 (d, 2H, J=7.16 Hz), 7.46 (d, 2H, J=7.27 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 191.80, 145.84, 138.10, 135.35, 134.70, 130.34, 129.20, 128.58, 127.51. GC/MS(EI): m/z 216 (M+), 218, 152.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-ed4a9ac1d9914854a4dd951dc781aa9b
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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