Acetyl chloride → Methyl 3-cyano-4-fluorobenzoate

HRID 1041853Notes

Reaction equation

HRID 1041853 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[F:12])[C:6]([OH:8])=[O:7])#[N:2].[C:13](Cl)(=O)C>CO>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([F:12])=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 27739323-Cyano-4-fluorobenzoic acid

Product 1

HCID 45790123Methyl 3-cyano-4-fluorobenzoateYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 16.0 g (96.9 mmol) 2a and 161 ml methanol were added 30.4 g (387.6 mmol) acetyl chloride drop wisely at 0° C. The reaction mixture was stirred over night, filtered and concentrated. The residue was diluted with dichloromethane, washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The residue was purified by column chromatography (hexane:ethylacetate). The desired product 2b was obtained in 78.1% yield (13.5 g; 75.7 mmol)

Workup

  1. customdrop wisely at 0° C
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionThe residue was diluted with dichloromethane
  5. washwashed with diluted sodium hydrogen carbonate solution
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (hexane:ethylacetate)

Sources & evidence

ORD record
ord-a6186fa964304221bdaa232d03d2a949
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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