Acetic Acid → Methyl 4-fluoro-3-(trifluoromethyl)benzoate

HRID 467448Notes

Reaction equation

HRID 467448 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[Si](C=[N+]=[N-])(C)(C)[CH3:16].C(O)(=O)C>CO.C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 5222684-Fluoro-3-(trifluoromethyl)benzoic acid

Product 1

HCID 15285559Methyl 4-fluoro-3-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-fluoro-3-(trifluoromethyl)benzoic acid (260 mg, 1.25 mmol, 1 eq) in MeOH (0.5 mL) and CH2Cl2 (2 mL) was treated with TMSCHN2 (2M in hexanes, 0.85 mL, 1.70 mmol, 1A eq) dropwise with stirring at room temperature. After the reaction was stirred for 10 min, acetic acid was added until the yellow color disappeared. The mixture was concentrated to afford methyl 4-fluoro-3-(trifluoromethyl)benzoate, which was used in the next step without further purification.

Workup

  1. stirringAfter the reaction was stirred for 10 min
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-98ba5fea4a8742f9ab5679667ab9d865
Source dataset
uspto-grants-2014_01
Patent number
US08623818B2

Reaction notes

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