2-Bromotoluene → 2,2'-Dimethylbiphenyl

HRID 412819

Reaction equation

HRID 412819 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.[F-].[K+]>C1COCC1>[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8]

Participants

5

Reactant 3

HCID 72362-BromotolueneHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 117972,2'-DimethylbiphenylYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromotoluene (87 mg, 0.51 mmol) reacted with 2-methylphenylboronic acid (88 mg, 0.65 mmol) using 1 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.50 mmol) in THF solvent at room temperature to give the title compound (91 mg, 98%) as a colorless oil: 1H-NMR (300 MHz, CDCl3): δ 7.29-7.35 (m, 6H), 7.20 (d, 2H, J=6.3 Hz), 2.15 (s, 6H).). 13C{1H}-NMR (100 MHz, CDCl3): δ 141.56, 135.76, 129.77, 129.25, 127.12, 125.51, 19.81. GC/MS(EI): m/z 182 (M+).

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-40b553aec2194ce18bed40f417ad18bc
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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