Methyl 2-bromobenzoate → Methyl 2-(4-formylphenyl)benzoate

HRID 1594187Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][C:6](OB(O)O)=[CH:5][CH:4]=1)=[O:2].[CH3:13][O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1Br.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 4-formylphenylboric acid (6.7 g) in N,N-dimethylformamide (100 ml) were added 2-bromobenzoic acid methyl ester (6.5 g), tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] (1.0 g) and tripotassium phosphate (23 g). The reaction mixture was stirred for 5 hours at 75° C. The reaction mixture was filtrated and concentrated. To the residue were added 1N hydrochloric acid and ethyl acetate, and the mixture was concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1) to give the title compound (4.1 g) having the following physical data.

Workup

filtrationThe reaction mixture was filtrated
concentrationconcentrated
additionTo the residue were added 1N hydrochloric acid and ethyl acetate
concentrationthe mixture was concentrated
customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-06d6b051a5e24121b349c0301dee4eec
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07300917B2

Reaction notes

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