1-Bromo-4-chloro-2-fluorobenzene → Bis(4-chloro-2-fluorophenyl)methanol

HRID 561502Notes

Reaction equation

HRID 561502 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[C:4]([F:9])[CH:3]=1.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[C:13]([F:19])[CH:12]=1.ClC1C=CC(C(C2C=CC(OC)=CC=2)O)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:15]([C:14]2[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][C:13]=2[F:19])[OH:16])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 3

HCID 1372751-Bromo-4-chloro-2-fluorobenzeneHCID 27249084-Chloro-2-fluorobenzaldehydeHCID 2757631(4-Chlorophenyl)(4-methoxyphenyl)methanol

Product 1

HCID 58392492Bis(4-chloro-2-fluorophenyl)methanol

Procedure

The title compound was prepared starting from 5.00 g (23.87 mmol) of 4-chloro-2-fluorobromobenzene and 4.54 g (28.65 mmol) of 4-chloro-2-fluorobenzaldehyde in analogy to the synthesis of the compound from Example 175A. A difference was that a preliminary separation by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient) was carried out before the purification of the crude product by preparative HPLC. 1.79 g (26% 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 gradient)
  3. customwas carried out before the purification of the crude product by preparative HPLC

Sources & evidence

ORD record
ord-a95bd9b6e25a410ba3ebfb6d98c795f6
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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