Cesium carbonate → 1-[4-(4-Trifluoromethyl-benzyloxy)-phenyl]-propan-2-one

HRID 1183350Notes

Reaction equation

HRID 1183350 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21](=[O:23])[CH3:22])=[CH:18][CH:19]=2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 665776531-[4-(4-Trifluoromethyl-benzyloxy)-phenyl]-propan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Bromomethyl-4-trifluoromethyl-benzene (1.55 g, 6.49 mmol) and 1-(4-hydroxy-phenyl)-propan-2-one (1.46 g, 9.74 mmol) were stirred in acetonitrile (65 mL) along with cesium carbonate (5.3 g, 16.23 mmol). After stirring at room temperature for two days the reaction was heated to 60° C. for 3 hours. After cooling the reaction was submitted to standard aqueous workup then purified on silica gel (0-100% (2% MeOH in EtOAC) to hexanes) to yield the title compound.

Workup

  1. temperaturewas heated to 60° C. for 3 hours
  2. temperatureAfter cooling the reaction
  3. customthen purified on silica gel (0-100% (2% MeOH in EtOAC) to hexanes)

Sources & evidence

ORD record
ord-c31e066fde1942219c5a7226535230ba
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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