Thionyl Chloride → 2-(2-Fluorophenyl)acetyl chloride

HRID 566260Notes

Reaction equation

HRID 566260 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.O=S(Cl)[Cl:14]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([Cl:14])=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67979Benzeneacetic acid, 2-fluoro-

Product 1

HCID 140040112-(2-Fluorophenyl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-fluorophenylacetic acid (450 g, 3.0 mol) in CH2Cl2 (900 mL) is added SOCl2 (714 g, 6 mol) dropwise. After addition is complete, the reaction mixture is heated to reflux for 2 hours. Subsequently, the solvent is removed in vacuo after which vacuum distillation of the resulting oil provides 2-fluorobenzeneacetyl chloride.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux for 2 hours
  4. customSubsequently, the solvent is removed in vacuo
  5. distillationafter which vacuum distillation of the resulting oil

Sources & evidence

ORD record
ord-0085fa34a5ab406aba87447bb04026e8
Source dataset
uspto-grants-2001_01
Patent number
US06174888B1

Reaction notes

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