Toluene → Methyl 2'-formyl-6'-methylbiphenyl-3-carboxylate

HRID 2422271Notes

Reaction equation

Br[C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:19]1(C)[CH:24]=[CH:23]C=[CH:21][CH:20]=1.[C:26]([O:29][CH2:30]C)(=[O:28])[CH3:27]>C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:10])[C:2]=1[C:20]1[CH:19]=[CH:24][CH:23]=[C:27]([C:26]([O:29][CH3:30])=[O:28])[CH:21]=1)=[O:5]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-bromo-3-methylbenzaldehyde (0.30 g, 1.51 mmol), tris(dibenzylidenacetone)dipalladium (0) (0.055 g, 0.060 mmol), 2-(dicyclohexylphosphino)biphenyl (0.032 g, 0.091 mmol), tripotassium phosphate (0.64 g, 3.0 mmol), 3-(methoxycarbonylphenyl)boronic acid (0.35 g, 1.96 mmol) and toluene (6 mL) was stirred under an argon atmosphere at 90° C. for 17 hrs. The reaction mixture was cooled, diluted with ethyl acetate, washed with water and saturated brine, dried (anhydrous sodium sulfate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=4/1) to give the title compound (0.25 g, yield 65%) as a yellow oil.

Workup

temperatureThe reaction mixture was cooled
washwashed with water and saturated brine
dry with materialdried (anhydrous sodium sulfate)
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-de985de72757433ab7b3fdf60489c6d3
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960369B2

Reaction notes

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