Ethyl Acetate → 1-[(Prop-2-en-1-yl)oxy]-4-[(trifluoromethyl)sulfanyl]benzene

HRID 2113150Notes

Reaction equation

HRID 2113150 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([F:4])[F:3].[C:13]([O-])([O-])=O.[Cs+].[Cs+].C(O[CH2:23][CH3:24])(=O)C>CN(C=O)C>[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:23]=[CH2:24])=[CH:8][CH:7]=1)([F:4])[F:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 38151584-(Trifluoromethylsulfanyl)phenol

Product 1

HCID 690500301-[(Prop-2-en-1-yl)oxy]-4-[(trifluoromethyl)sulfanyl]benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-(trifluoromethylsulfanyl)phenol (1.9 g, 10 mmol), allyl brimide (1.8 g, 15 mmol) and Cs2CO3 (6.5 g, 20 mmol) in DMF, 80 mL) was stirred for 2 hrs at 50° C. The reaction was diluted with ethyl acetate and washed with water. The organic phase was dried and concentrated to give essentially pure allyl 4-(trifluoromethylsulfanyl)phenyl ether.

Workup

  1. washwashed with water
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3f5b31533c4140eb8dcadd2d494bf0fc
Source dataset
uspto-grants-2009_04
Patent number
US07524882B2

Reaction notes

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