Thionyl Chloride → 4-Bromo-2,5-difluorobenzoic acid chloride

Reaction equation

[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([F:12])[CH:3]=1.S(Cl)([Cl:15])=O>>[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 8228574-Bromo-2,5-difluorobenzoic acid

Product 1

HCID 103776784-Bromo-2,5-difluorobenzoic acid chlorideYield 91%

Conditions

Temperature: 90 °C

Procedure

A total of 2075 g (8.79 moles) of crude 4-bromo-2,5-difluorobenzoic acid from step (b) was treated with thionyl chloride (2.0 L), and the resulting slurry was slowly heated to reflux (90° C. internal) to obtain a solution. After removal of excess thionyl chloride, the product was collected at 85°-95° C. (oil pump, vacuum not measured), leaving a solid residue. The distillate afforded 2045 g (91%) of a liquid which was used directly in the next step.

Workup

temperaturethe resulting slurry was slowly heated
customto obtain a solution
customAfter removal of excess thionyl chloride
customthe product was collected at 85°-95° C. (oil pump, vacuum not
customleaving a solid residue

Sources & evidence

ORD record: ord-bae4f905426942e58e7b610af1aac79a
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075319

Reaction notes

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