4-Chlorobenzaldehyde → 4-(2-Methylphenyl)benzaldehyde

HRID 412824Notes

Reaction equation

HRID 412824 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.[F-].[K+]>C1COCC1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH3:10])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 13936074-(2-Methylphenyl)benzaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorobenzaldehyde (144 mg, 1.02 mmol) reacted with 2-methylphenylboronic acid (204 mg, 1.50 mmol) using 1/2 mol % of Pd(OAc)2/Ph5FcP(t-Bu)2 and KF (180 mg, 3.10 mmol) in THF at 50° C. to give the title compound (189 mg, 96%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 9.98 (s, 1H), 7.85 (d, 2H, J=8.2 Hz), 7.41 (d, 2H, J=8.1 Hz), 7.22-7.13 (m, 4H), 2.19 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 191.98, 148.36, 140.51, 135.06, 134.87, 130.54, 129.88, 129.55, 129.42, 128.03, 125.94, 20.34. GC/MS(EI): m/z 196 (M+), 165, 167, 152. Anal. Calcd for C14H12O: C, 85.68; H, 6.16. Found: C, 85.64; H, 6.39.

Workup

  1. customat 50° C.

Sources & evidence

ORD record
ord-398b0435d1da4ce5af2aa535ab228b7f
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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