Thionyl Chloride → HCID 90315066, compound

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:20])=O>>[F:1][C:2]1[CH:10]=[C:9]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:20])=[O:5]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 469413502-Fluoro-4-(perfluoroethyl)benzoic acid

Product 1

HCID 90315066HCID 90315066, compoundYield 93.4%

Conditions

Temperature: 60 °C

Procedure

To 2-fluoro-4-(1,1,2,2,2-pentafluoroethyl)benzoic acid (1 g, 3.87 mmol) was added thionyl chloride (3.67 mL, 50.36 mmol) and the reaction was stirred at 60° C. for 22 hours. Excess thionyl chloride was removed in vacuo to yield 2-fluoro-4-(1,1,2,2,2-pentafluoroethyl)benzoyl chloride (1 g, 93%) as a viscous yellow liquid.

Workup

customExcess thionyl chloride was removed in vacuo

Sources & evidence

ORD record: ord-474a27e6b3d744aea3c360023f7d21a8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09421196B2

Reaction notes

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