P-Chloroacetophenone → 1-(4-Chlorophenyl)-1-(4-fluorophenyl)ethanol

HRID 561505Notes

Reaction equation

HRID 561505 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][CH:13]=1)=[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])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 99931-Bromo-4-fluorobenzeneHCID 2757452(4-Chloro-3-fluorophenyl)(4-fluorophenyl)methanol

Product 1

HCID 135116831-(4-Chlorophenyl)-1-(4-fluorophenyl)ethanol

Procedure

The title compound was prepared starting from 5.00 g (28.57 mmol) of 4-bromofluorobenzene and 4.86 g (31.43 mmol) of 4-chloroacetophenone in analogy to the synthesis of the compound from Example 176A. A difference was that a preliminary separation by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9/1) was carried out before the purification of the crude product by preparative HPLC. 5.23 g (73% of theory) of the title compound were obtained.

Workup

  1. customThe title compound was prepared
  2. customA difference was that a preliminary separation by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9/1)
  3. customwas carried out before the purification of the crude product by preparative HPLC

Sources & evidence

ORD record
ord-4b42cca7cde04409ae14b93ce136d676
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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