3,4-Dichlorobenzyl chloride → 4-(3,4-Dichlorophenyl)-3-(2-fluoro-4-biphenylyl)-2-butanone

HRID 1452424Notes

Reaction equation

HRID 1452424 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22]Cl.[OH-].[Na+]>>[Cl:18][C:19]1[CH:20]=[C:21]([CH2:22][CH:8]([C:6]2[CH:5]=[CH:4][C:3]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:2]([F:1])[CH:7]=2)[C:9](=[O:11])[CH3:10])[CH:24]=[CH:25][C:26]=1[Cl:27]

Participants

4

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 129504182-Fluoro-4-biphenylyl acetone

Product 1

HCID 190736134-(3,4-Dichlorophenyl)-3-(2-fluoro-4-biphenylyl)-2-butanoneYield 85%

Conditions

Temperature
100 °C

Procedure

45.1 g of the ketone compound thus obtained, 50.3 g of 3,4-dichlorobenzyl chloride and 15.8 g of sodium hydroxide were mixed, heated with stirring at 100° C. for 6 hours. The reaction solution was left to cool to room temperature and then extracted by an addition of ethyl acetate and water. The organic layer was post-treated by a conventional method. Then, the product was purified by silica gel column chromatography (hexane/ethyl acetate=50/1) to obtain 65.0 g (yield: 85%) of 4-(3,4-dichlorophenyl)-3-(2-fluoro-4-biphenylyl)-2-butanone.

Workup

  1. temperatureheated
  2. waitThe reaction solution was left
  3. temperatureto cool to room temperature
  4. extractionextracted by an addition of ethyl acetate and water
  5. additionThe organic layer was post-treated by a conventional method
  6. customThen, the product was purified by silica gel column chromatography (hexane/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-ab58da38e8584aa0b20178880389b094
Source dataset
uspto-grants-1997_02
Patent number
US05606101

Reaction notes

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