Sodium Carbonate → 4-(4-Methylpyridin-2-yl)benzaldehyde

HRID 1059989Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[CH:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:14]2[CH:15]=[CH:16][C:11]([CH:9]=[O:10])=[CH:12][CH:13]=2)[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 2-bromo-4-methylpyridine (2.0 g), 4-formylphenylboronic acid (2.27 g) and tetrakis(triphenylphosphine)-palladium (0.67 g) in 1,2-dimethoxyethane (40 ml) was added 2M aqueous solution of sodium carbonate (15.1 ml). The mixture was stirred at 90° C. for 6 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 75 g, dichloromethane) to give 4-(4-methylpyridin-2-yl)benzaldehyde (483 mg).

Workup

temperaturecooled to room temperature
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography (silica gel 75 g, dichloromethane)

Sources & evidence

ORD record: ord-a78fde7a720d41208c5dc90c0be66d12
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521643B1

Reaction notes

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