4-Fluorobenzoic Acid → 4-Fluorobenzoic acid, 3-fluorophenyl ester

HRID 247186

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1>COCCOCCOCCOCCOC>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][C:4]2[CH:5]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 240 °C

Procedure

A 25-ml Kjeldahl flask fitted with an air-cooling line was charged with 1.4 g of p-flurobenzoic acid, 0.976 g of cupric hydroxide, and 3 ml of tetraglyme as solvent, after which it was heated at 240° C. over an oil bath. This temperature was maintained for 60 minutes. After cooling, the reaction mixture was eluted with diethyl ether followed by filtration using Celite. the resulting filtrate was then submitted to column chromatography (solid phase: silica gel, developing solvent: hexane→methylene chloride) to give 0.013 g of m-fluorophenyl p-fluorobenzoate.

Workup

customA 25-ml Kjeldahl flask fitted with an air-cooling line
temperatureThis temperature was maintained for 60 minutes
temperatureAfter cooling
washthe reaction mixture was eluted with diethyl ether
filtrationfollowed by filtration

Sources & evidence

ORD record: ord-e7eec9de80b243ba891dc68229b2903d
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04705884

Linked notes

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