Diazomethane → Benzoic acid, 3-fluoro-, methyl ester

HRID 867791Notes

Reaction equation

HRID 867791 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[N+](=[CH2:13])=[N-]>CCOCC>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:13])=[O:6]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 99683-Fluorobenzoic Acid

Product 1

HCID 521184Benzoic acid, 3-fluoro-, methyl esterYield 84.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ice-cooled and stirred solution of m-fluorobenzoic acid (8.0 g, 57 mmol) in 50 ml of ether was added an excess solution of diazomethane in ether. After concentration, the residue was distilled under reduced pressure to give a colorless transparent oil of methyl m-fluorobenzoate (7.4 g, 48.1 mmol, yield 84.4%, b.p. 80°-82° C./16 mmHg), which was assigned the structure by the following data:

Workup

  1. concentrationAfter concentration
  2. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-5404a5312f7d4bfd867809542dc99ecb
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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