2-Bromoanisole → HCID 11448114, compound

HRID 412811Notes

Reaction equation

HRID 412811 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.[F-].[K+]>C1COCC1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:15]1[CH:16]=[CH:17][C:12]([C:11]([F:22])([F:21])[F:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 113582-BromoanisoleHCID 522689Potassium FluorideHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 11448114HCID 11448114, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromoanisole (98 mg, 0.52 mmol) reacted with 4-trifluoromethylphenylboronic acid (145 mg, 0.76 mmol) using 1 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (90 mg, 1.55 mmol) in THF at room temperature for 3 h to give the title compound (128 mg, 97%). 1H-NMR (300 MHz, CDCl3): δ 13C{1H}-NMR (100 MHz, CDCl3): δ. GC/MS(EI): m/z (M+).

Workup

  1. customat room temperature
  2. customfor 3 h

Sources & evidence

ORD record
ord-8a03704e06974ec0aec25dacc6e6d3ae
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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