2-Bromoanisole → 4'-Chloro-2-methoxy-1,1'-biphenyl

HRID 412812Notes

Reaction equation

HRID 412812 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[F-].[K+]>C1COCC1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:14]1[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 113582-BromoanisoleHCID 742994-Chlorophenylboronic acidHCID 522689Potassium Fluoride

Product 1

HCID 126485154'-Chloro-2-methoxy-1,1'-biphenylYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromoanisole (97 mg, 0.52 mmol) reacted with 4-chlorophenylboronic acid (102 mg, 0.65 mmol) using 0.5/1.0 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (8.8 mg, 1.57 mmol) in THF (2 ml) at room temperature to give the title compound (108 mg, 95%): 1H-NMR (400 MHz, CDCl3): δ 7.51 (d, 2H, J=8.4 Hz), 7.42 (d, 2H, J=8.0 Hz), 7.46-7.32 (m, 2H), 7.08 (t, 1H, J=7.6 Hz, aryl coupling J=1.2), 7.03 (d, 1H, J=8.0 Hz), 3.85 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 156.27, 136.86, 132.79, 130.81, 130.60, 129.33, 128.94, 128.10, 120.85, 111.16, 55.47. GC/MS(EI): m/z 218 (M+), 220 (M++2, Cl isotope peak), 168, 139. Anal. Calcd for C13H11ClO: C, 71.40; H, 5.07. Found: C, 71.47; H, 5.21.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-40c666cddfb8410bb055d83b419925d1
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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