Hexane → Methyl 2,3-difluoro-4-methylbenzoate

HRID 2261801Notes

Reaction equation

HRID 2261801 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Si](C=[N+]=[N-])(C)(C)[CH3:14].CCCCCC>C(Cl)Cl.CO>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([CH3:12])=[C:10]([F:11])[C:2]=1[F:1]

Participants

6

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 27741412,3-Difluoro-4-methylbenzoic acid

Product 1

HCID 55255640Methyl 2,3-difluoro-4-methylbenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-difluoro-4-methyl-benzoic acid (5.0 g, 29 mmol) in CH2Cl2 (20 mL) and MeOH (20 mL) is added 2.0 M TMSCHN2 in hexane (17.5 mL, 34.9 mmol) at 0° C. The reaction mixture is stirred for 1.0 h. The reaction mixture is concentrated to a residue and the residue is purified by flash chromatography to afford the title compound as an oil (5.7 g, 100%). LC-ES/MS m/e 208.3 (M+23).

Workup

  1. concentrationThe reaction mixture is concentrated to a residue
  2. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-c012a4255c2d486789dcc7a48d8d1ec1
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…