Thionyl Chloride → Fluorocinnamoyl chloride

HRID 652281Notes

Reaction equation

[F:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](O)=[O:4].S(Cl)([Cl:15])=O>>[F:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([Cl:15])=[O:4]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 98321Fluorocinnamic acid

Product 1

HCID 54157638Fluorocinnamoyl chloride

Conditions

Temperature: 80 °C

Procedure

To α-fluorocinnamic acid (5.48 g, 33 mM), thionyl chloride (40 ml) was added, and the thus obtained mixture was stirred at 80° C. under refluxing for 2 hours. After cooling it to a room temperature, the unreacted thionyl chloride was distilled off under reduced pressure to give a syrup-like α-fluorocinnamoyl chloride.

Workup

temperatureunder refluxing for 2 hours
temperatureAfter cooling it to a room temperature
distillationthe unreacted thionyl chloride was distilled off under reduced pressure

Sources & evidence

ORD record: ord-1abb513cbbea41038d3b74bfe741a245
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04670584

Reaction notes

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