Thionyl Chloride → 4-(Trifluoromethyl)cinnamoyl chloride

HRID 322007

Reaction equation

HRID 322007 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9](O)=[O:10])=[CH:5][CH:4]=1.S(Cl)([Cl:18])=O>CN(C=O)C>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([Cl:18])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 6880704-(Trifluoromethyl)cinnamic acid

Product 1

HCID 111072914-(Trifluoromethyl)cinnamoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
75 °C

Procedure

200.0 mg (0.92 mmol) of trans-4-trifluoromethylcinnamic acid were treated with 200 μl of thionyl chloride. After addition of 2 drops of DMF, the reaction solution obtained was stirred at 75° C. for 3 h. It was then concentrated to dryness, and the residue was taken up in toluene 2× and concentrated to dryness again. Drying in a high vacuum yielded 237.0 mg of the title compound as a slightly yellow, amorphous powder.

Workup

  1. customthe reaction solution obtained
  2. concentrationIt was then concentrated to dryness
  3. concentrationconcentrated to dryness again
  4. customDrying in a high vacuum

Sources & evidence

ORD record
ord-fc6c1c230be84f99a7c445e3d7914d02
Source dataset
uspto-grants-2001_04
Patent number
US06211196B1

Linked notes

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