Ammonium Chloride → (5-Bromo-2,4-difluoro-phenyl)-(3-fluoro-phenyl)-methanol

HRID 1983502Notes

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.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21].[Cl-].[NH4+]>C(OCC)C.CCCCCC>[Br:8][C:6]1[C:5]([F:9])=[CH:4][C:3]([F:10])=[C:2]([CH:20]([C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([F:16])[CH:18]=2)[OH:21])[CH:7]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A total of 2.02 g of 1,5-dibromo-2,4-difluorobenzene obtained in Production Example II-5-a was dissolved in 38 ml of diethyl ether, and 4.9 ml of a 1.58 M solution of n-butyllithium in hexane was added under stirring at −70° C. After stirring for 1 hour, 4.9 ml of m-fluorobenzaldehyde was added and the mixture was stirred for 15 minutes. Saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extracting with ethyl acetate. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:10), to give 0.96 g of the title compound.

Workup

stirringAfter stirring for 1 hour
stirringthe mixture was stirred for 15 minutes
extractionby extracting with ethyl acetate
washThe resulting organic layer was washed with brine
dry with materialdried over magnesium sulfate
customthe solvent was evaporated
customThe residue was purified
customseparated by silica gel column chromatography (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record: ord-7dd4ed8f1fbd4bcb81d43c4c8aa86915
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541376B2

Reaction notes

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