4-Chloro-3-(trifluoromethyl)phenol → 4-(4-Chloro-3-trifluoromethyl-phenoxy)-3-fluoro-benzaldehyde

HRID 705833Notes

Reaction equation

HRID 705833 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1F)[CH:17]=[O:18]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:21]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=2[F:13])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

3

Reactant 2

HCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 866661984-(4-Chloro-3-trifluoromethyl-phenoxy)-3-fluoro-benzaldehydeYield 80.2%

Conditions

Temperature
80 °C

Procedure

The mixture of 4-chloro-3-(trifluoromethyl)phenol (7.61 g, 38.7 mmol), 3,4-difluorobenzaldehyde (5.0 g, 35.2 mmol) and CS2CO3 (11.46 g, 35.2 mmol) was heated with a microwave reactor at 80° C. for 1 h. Purification via a flash column chromatography then afforded the title compound (9.0 g, 80% yield). LCMS: rt=3.80 min, [M+H+]=319

Workup

  1. customPurification via a flash column chromatography

Sources & evidence

ORD record
ord-3c1cece4f79b4c268fe9a14f5b3957a9
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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