Dimethylformamide → 5-Bromo-2,4-difluorobenzaldehyde

HRID 503187Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([Br:8])[C:5]([F:9])=[CH:4][C:3]=1[F:10].C([Li])CCC.CN(C)[CH:18]=[O:19]>>[Br:8][C:6]1[C:5]([F:9])=[CH:4][C:3]([F:10])=[C:2]([CH:7]=1)[CH:18]=[O:19]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 105645111,5-Dibromo-2,4-difluorobenzene

HCID 178418339Butyllithium

Product 1

HCID 222607695-Bromo-2,4-difluorobenzaldehyde

Procedure

As a raw material, 17.7 g of 1,5-dibromo-2,4-difluorobenzene obtained in Production Example II-5-a was subjected to lithiation with n-butyllithium by the procedure of Production Example II-5-b, was subjected to formylation with N,N-dimethylformamide, to give 10.7 g of 5-bromo-2,4-difluorobenzaldehyde. This compound was allowed to react with benzothiophene by the procedure of Production Example II-12-a to yield an alcohol, and then the alcohol was oxidized by the procedure of Production Example II-10-b, to give 9.7 g of the title compound as a colorless oil.

Sources & evidence

ORD record: ord-c6f49d5d15e84c2c9d5aa660b4786f40
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776890B2

Reaction notes

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