3,5-Dichlorobenzaldehyde → 3-(3,5-Dichlorobenzylidene)-1,1,1-trifluoro-2,4-hexanedione

HRID 353090Notes

Reaction equation

HRID 353090 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH:16]=O>>[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH:16]=[C:4]([C:5](=[O:8])[CH2:6][CH3:7])[C:3](=[O:9])[C:2]([F:10])([F:11])[F:1]

Participants

3

Reactant 2

HCID 357463,5-DichlorobenzaldehydeHCID 678642,4-Hexanedione, 1,1,1-trifluoro-

Product 1

HCID 695545523-(3,5-Dichlorobenzylidene)-1,1,1-trifluoro-2,4-hexanedione

Procedure

The title compound was prepared by a similar method to that of Preparation 9 using 1,1,1-trifluorohexane-2,4-dione and 3,5-dichlorobenzaldehyde. The crude product was purified by flash chromatography on silica gel eluting with a solvent gradient of pentane gradually changing to pentane:ethyl acetate (5:1, by volume). The product was further purified by flash chromatography eluting with dichloromethane:pentane (1:10, by volume) to afford a mixture of the title compounds (500 mg) as a yellow oil.

Workup

  1. customThe crude product was purified by flash chromatography on silica gel eluting with a solvent gradient of pentane
  2. customThe product was further purified by flash chromatography
  3. washeluting with dichloromethane:pentane (1:10, by volume)
  4. customto afford

Sources & evidence

ORD record
ord-2fa26870d5874cc29a5f81fb522699f1
Source dataset
uspto-grants-2004_06
Patent number
US06750230B2

Reaction notes

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