Acetyl chloride → HCID 66909120, compound

HRID 1041871Notes

Reaction equation

HRID 1041871 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13].[C:16](Cl)(=O)C>CO>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([O:11][C:12]([F:14])([F:13])[F:15])[CH:4]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 177507774-Fluoro-3-(trifluoromethoxy)benzoic acid

Product 1

HCID 66909120HCID 66909120, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 21.2 g (96.9 mmol) 4-Fluoro-3-trifluoromethoxy-benzoic acid (JRD-Fluoro) 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 14a was obtained in 75% yield (17.3 g; 72.7 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-053d53668dbd4344b507744711ca611e
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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