Chlorotrimethylsilane → 2-Chloro-5-fluoro-4-methyl-3-nitro-benzoic acid methyl ester

HRID 1697342Notes

Reaction equation

HRID 1697342 reaction equation
Cl[Si](C)(C)[CH3:3].[Cl:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([CH3:19])[C:13]([F:20])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]>CO.O>[CH3:3][O:10][C:9](=[O:11])[C:8]1[CH:12]=[C:13]([F:20])[C:14]([CH3:19])=[C:15]([N+:16]([O-:18])=[O:17])[C:7]=1[Cl:6]

Participants

5

Reactant 2

HCID 6397Chlorotrimethylsilane2×HCID 136574392-Chloro-5-fluoro-4-methyl-3-nitro-benzoic acid

Product 1

HCID 866615862-Chloro-5-fluoro-4-methyl-3-nitro-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A solution of chlorotrimethylsilane (200 mL) in methanol (300 mL) was treated with 2-chloro-5-fluoro-4-methyl-3-nitrobenzoic acid (Example 252c, 65.5 g) portionwise under nitrogen. The resulting solution was stirred at 20° C. for 16 h. Further chlorotrimethylsilane (100 mL) was added and the reaction heated at 50° C. for 6 h. The reaction mixture was evaporated to afford crude product which was diluted with water and extracted with ethyl acetate (300 mL). The organic extract was dried (MgSO4), filtered and evaporated to afford the subtitle compound (53.4 g).

Workup

  1. temperaturethe reaction heated at 50° C. for 6 h
  2. customThe reaction mixture was evaporated
  3. customto afford crude product which
  4. extractionextracted with ethyl acetate (300 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ffc4692bbc0e478fa8672a68cfdf6c3c
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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