Trimethylsilyldiazomethane → Methyl 4-fluoro-2-(trifluoromethyl)benzoate

HRID 1946326Notes

Reaction equation

HRID 1946326 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:16]>CO.C(Cl)(Cl)Cl.CCOCC>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[C:4]([C:11]([F:12])([F:13])[F:14])[CH:3]=1

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 6882554-Fluoro-2-(trifluoromethyl)benzoic acid

Product 1

HCID 15541084Methyl 4-fluoro-2-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4-fluoro-2-(trifluoromethyl)benzoic acid (2.02 g, 9.71 mmol, Aldrich) in methanol and chloroform (1:1, 32 ml) was added a 2 M TMS-diazomethane in ether (˜7 ml) in portions, over about 2 h, allowing the solution to cool down between additions. The solution was evaporated in vacuo and the residue dissolved in chloroform (˜20 ml). The solution was evaporated in vacuo to give methyl 4-fluoro-2-(trifluoromethyl)benzoate as a slightly yellow-brown liquid (2.07 g).

Workup

  1. temperatureto cool down between additions
  2. customThe solution was evaporated in vacuo
  3. dissolutionthe residue dissolved in chloroform (˜20 ml)
  4. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-6ffda50b72904b938d1c859ad3fe98c7
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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