Methyl 4-chlorobenzoate → Methyl 4-(2-methylphenyl)benzoate

HRID 412828Notes

Reaction equation

HRID 412828 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.[F-].[K+]>C1COCC1>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH3:12])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 14307Methyl 4-chlorobenzoateHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 1392850Methyl 4-(2-methylphenyl)benzoateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-chlorobenzoate (172 mg, 1.01 mmol) reacted with 2-methylphenylboronic acid (210 mg, 1.54 mmol) using 1/2 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (190 mg, 3.39 mmol) in THF at 100° C. to give the title compound (209 mg, 92%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 8.13 (d, 2H, J=8.24 Hz), 7.44 (d, 2H, J=8.20 Hz), 7.33-7.25 (m, 4H), 3.98 (s, 3H), 2.30 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 166.98, 146.69, 140.79, 135.10, 130.44, 129.47, 129.36, 129.21, 128.53, 127.78, 125.85, 52.06, 20.33. GC/MS(EI): m/z 226 (M+), 195, 165, 152. Anal. Calcd for C15H14O2: C, 79.62; H, 6.24. Found C, 79.33; H, 6.26.

Workup

  1. customat 100° C.

Sources & evidence

ORD record
ord-ade935c92689409f83d6458e930cc0a0
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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