Thionyl Chloride → 2-(4-(Trifluoromethyl)phenyl)acetyl chloride

HRID 1616968Notes

Reaction equation

HRID 1616968 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[CH:5][CH:4]=1.S(Cl)([Cl:17])=O>>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([Cl:17])=[O:11])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid

Product 1

HCID 148109432-(4-(Trifluoromethyl)phenyl)acetyl chloride

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, to 4-trifluoromethylphenylacetic acid (51) (817 mg, 4.00 mmol) was added thionyl chloride (5.00 mL, 68.9 mmol), and heated to reflux (100° C.) for 1.5 h. After cooling to room temperature, the mixture was concentrated under reduced pressure to give 4-trifluoromethylphenylacetyl chloride (52) as a brown oily crude product, which was used in the next reaction without further purification.

Workup

  1. temperatureheated
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d28c7284a7c64b1d86725f0656ec8717
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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