2,2-Difluoro-2-phenylethanol → (2-((6-Bromohexyl)oxy)-1,1-difluoroethyl)benzene

Reaction equation

[F:1][C:2]([F:11])([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]OCC(F)(F)CCC1C=CC=CC=1>>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:4][CH2:3][C:2]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)([F:11])[F:1]

Participants

Reactant 2

HCID 97938912,2-Difluoro-2-phenylethanol

HCID 67246468{4-((6-Bromohexyl)oxy]-3,3-difluorobutyl}benzene

Product 1

HCID 67245921(2-((6-Bromohexyl)oxy)-1,1-difluoroethyl)benzeneYield 78%

Procedure

Obtained from Intermediate 6 (6.88 g, 43.5 mmol) by the procedure described in Intermediate 3. Purification by column chromatography with silica gel and n-hexane/ethyl acetate (10:1) as eluent gave the title compound (10.9 g, 78%) as oil.

Workup

customPurification by column chromatography with silica gel and n-hexane/ethyl acetate (10:1) as eluent

Sources & evidence

ORD record: ord-7b01e0f342864953be621e60e31b27d6
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242177B2

Reaction notes

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