1-Bromo-4-fluorobenzene → 1-(4-Chloro-2-fluorophenyl)-1-(4-fluorophenyl)ethanol

HRID 561506Notes

Reaction equation

HRID 561506 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[F:19])=[O:11].ClC1C=CC(C(C2C=CC(F)=CC=2)O)=CC=1F>>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]([C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=2)([OH:11])[CH3:9])=[C:13]([F:19])[CH:14]=1

Participants

4

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 2757452(4-Chloro-3-fluorophenyl)(4-fluorophenyl)methanolHCID 150305521-(4-Chloro-2-fluorophenyl)ethan-1-one

Product 1

HCID 583924191-(4-Chloro-2-fluorophenyl)-1-(4-fluorophenyl)ethanol

Procedure

The title compound was prepared starting from 4.22 g (24.14 mmol) of 4-bromofluorobenzene and 5.00 g (28.97 mmol) of 4-chloro-2-fluoroacetophenone in analogy to the synthesis of the compound from Example 176A. A difference was that the crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9/1). 5.23 g (73% of theory) of the title compound were obtained.

Workup

  1. customThe title compound was prepared
  2. customwas purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-658db080808547a094883e66a03bce51
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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