Thionyl Chloride → 3,4-Difluorophenylacetyl chloride

HRID 1867299Notes

Reaction equation

HRID 1867299 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[F:8].S(Cl)([Cl:15])=O>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([Cl:15])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69571(3,4-Difluorophenyl)acetic acid

Product 1

HCID 146180853,4-Difluorophenylacetyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To (3,4-difluoro-phenyl)-acetic acid (2.0 g) dissolved in 1,2-dichloroethane (5 mL) was added thionyl chloride (5 mL) and the mixture was refluxed for 16 hours under argon. The crude mixture was concentrated in vacuo to furnish 2.2 g (100%) of the title compound as a yellow oil. 1H NMR (500 MHz, CDCl3): 4.10 (s, 2H), 7.00 (m, 1H), 7.11 (m, 1H), 7.17 (m, 1H).

Workup

  1. temperaturethe mixture was refluxed for 16 hours under argon
  2. concentrationThe crude mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-39c4fa9e1ad942f0ad54f54dcf9e333a
Source dataset
uspto-grants-2009_12
Patent number
US07632835B2

Reaction notes

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