4-Chlorobenzaldehyde → (1,1'-Biphenyl)-4-carboxaldehyde

HRID 412825Notes

Reaction equation

HRID 412825 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[F-].[K+]>C1COCC1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

Product 1

HCID 76689(1,1'-Biphenyl)-4-carboxaldehydeYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorobenzaldehyde (144 mg, 1.02 mmol) reacted with phenylboronic acid (185 mg, 1.36 mmol) using 1/2 mol % of Pd(OAc)2/Ph5FcP(t-Bu)2 and KF (178 mg, 3.18 mmol) in THF at 50° C. to give the title compound (180 mg, 96%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 8.05 (s, 1H), 7.96 (d, 2H, J=8.32 Hz), 7.76 (d, 2H, J=8.22 Hz), 7.65 (d, 2H, J=7.08 Hz), 7.52-7.14 (m, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 191.88, 147.10, 139.62, 135.11, 130.21, 128.96, 128.42, 127.61, 127.30. GC/MS(EI): m/z 182 (M+), 152. Anal. Calcd for C13H10O: C, 85.69; H. 5.53. Found: C, 85.69; H, 5.77.

Workup

  1. customat 50° C.

Sources & evidence

ORD record
ord-2d08295265a945f59e39a85914ccef7d
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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