Bromobenzene → 2-Methylbiphenyl

HRID 412805

Reaction equation

HRID 412805 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.[F-].[K+]>C1COCC1>[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 125632-MethylbiphenylYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromobenzene (80 mg, 0.51 mmol) reacted with 2-methylphenylboronic acid (90 mg, 0.66 mmol) using 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 (80 mg, 95%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 7.51-7.47 (m, 2H), 7.44-7.40 (m, 3H), 7.36-7.32 (m, 4H), 2.36 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 141.91, 141.89, 135.30, 130.27, 129.76, 129.16, 128.03, 127.22, 126.72, 125.73, 20.46. GC/MS(EI): m/z 168 (M+), 153.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-febc04f39af74a9892aa859c2bae16a2
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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