Dimethylformamide → Ethyl 3-fluoro-2-methylbenzoate

HRID 477785Notes

Reaction equation

HRID 477785 reaction equation
[F:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:23][CH3:24])=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2466823-Fluoro-2-methylbenzoic acid

Product 1

HCID 14626272Ethyl 3-fluoro-2-methylbenzoateYield 93.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 10 g of 3-fluoro-2-methylbenzoic acid [J. Org. Chem., 26, 3208 (1961)]in 300 ml of dimethylformamide are added 30 g of potassium carbonate and 30 g of ethyl iodide and the mixture is stirred at room temperature for 8 hours. After adding 500 ml of toluene, washing with water and a saturated saline solution and drying over magnesium sulfate, the solvent is distilled off under reduced pressure to give 11 g of ethyl 3-fluoro-2-methylbenzoate (oil). Mass spectrum m/z: 182(M+).

Workup

  1. washwashing with water
  2. dry with materiala saturated saline solution and drying over magnesium sulfate
  3. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-e5a800762539454e9188c5139c31b007
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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