Carbon tetrabromide → 1-(3-Bromo-1,1-difluoropropyl)-4-fluorobenzene

HRID 1925536Notes

Reaction equation

Br[C:2]([Br:5])(Br)Br.[F:6][C:7]([F:18])([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[CH2:8]CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC.CC(=O)OCC>C(Cl)Cl.O>[Br:5][CH2:2][CH2:8][C:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([F:6])[F:18]

Participants

Conditions

Temperature: 0 °C

Procedure

3.1 g (9.5 mmol) of tetrabromomethane were added to a solution of 1.0 g (5.3 mmol) of 3,3-difluoro-3-(4-fluorophenyl)propan-1-ol in DCM (20 ml) and cooled to 0° C. At that temperature, 2.48 g (9.5 mmol) of triphenylphosphine were added in portions. Stirring was then carried out for 3 h at RT. The mixture was then diluted with water (50 ml) and extracted with EA (3×60 ml). The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 24:1) of the residue yielded 1.25 g (5.0 mmol, 94%) of 1-(3-bromo -1,1-difluoropropyl)-4-fluorobenzene.

Workup

extractionextracted with EA (3×60 ml)
washThe combined organic phases were washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d7e7f7cc6abf42dda0d2a48087415902
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178684B2

Reaction notes

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