2-(4-Fluorophenyl)acetic acid → 4-Fluorophenylacetyl chloride

HRID 1388586Notes

Reaction equation

HRID 1388586 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:14])=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:14])=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 98372-(4-Fluorophenyl)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 37449884-Fluorophenylacetyl chloride

Procedure

p-Fluorophenylacetic acid (20 g) was stirred with thionyl chloride (30 ml) at room temperature for 5 hours. The excess of thionyl chloride was then removed under reduced pressure. The remaining oil was dissolved in toluene, and the toluene then removed under reduced pressure. The remaining oil was distilled (b.p. 41°-42°/0.1 mm) to give p-fluorophenylacetyl chloride (19.74 g).

Workup

  1. customThe excess of thionyl chloride was then removed under reduced pressure
  2. dissolutionThe remaining oil was dissolved in toluene
  3. customthe toluene then removed under reduced pressure
  4. distillationThe remaining oil was distilled (b.p. 41°-42°/0.1 mm)

Sources & evidence

ORD record
ord-a5e755f1a0cf4f3d9fe35dcc303cb2df
Source dataset
uspto-grants-1984_02
Patent number
US04431834

Reaction notes

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