2-(3-Bromophenyl)-2,2-difluoroethanol → 1-Bromo-3-{2-[(6-bromohexyl)oxy]-1,1-difluoroethyl}benzene

HRID 885547Notes

Reaction equation

HRID 885547 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([F:12])([F:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]OCC(F)(F)CCC1C=CC=CC=1>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:12])[CH2:9][O:10][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][Br:13])[CH:3]=1

Participants

3

Reactant 2

HCID 672463332-(3-Bromophenyl)-2,2-difluoroethanolHCID 67246468{4-((6-Bromohexyl)oxy]-3,3-difluorobutyl}benzene

Product 1

HCID 672452111-Bromo-3-{2-[(6-bromohexyl)oxy]-1,1-difluoroethyl}benzene

Procedure

Obtained from Intermediate 49 (17.6 g, 74 mmol) by the procedure described in Intermediate 3. The crude oil was purified by distillation to yield the title compound as oil of 60% of purity (9.5 g). The distillation residue was purified by column chromatography with silica gel and methylene chloride as eluent to yield a second batch of 1-bromo-3-{2-[(6-bromohexyl)oxy]-1,1-difluoroethyl}benzene of 65% of purity (15.2 g) (overall yield: 53%).

Workup

  1. distillationThe crude oil was purified by distillation

Sources & evidence

ORD record
ord-f30c18b5f0e9438ea101a29d20588bd2
Source dataset
uspto-grants-2012_08
Patent number
US08242177B2

Reaction notes

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