Chlorotrimethylsilane → Methyl 2,5-difluoro-3-nitrobenzoate

HRID 2196639Notes

Reaction equation

HRID 2196639 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([F:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:15][Si](Cl)(C)C>CO>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([F:14])=[CH:7][C:3]=1[C:4]([O:6][CH3:15])=[O:5]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 156225272,5-Difluoro-3-nitrobenzoic acid

Product 1

HCID 43449027Methyl 2,5-difluoro-3-nitrobenzoateYield 72.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5-Difluoro-3-nitrobenzoic acid (2.00 g, 9.847 mmol) was dissolved in MeOH (60 mL). TMSCl (6.220 mL, 49.24 mmol) was added, and the reaction mixture was stirred at reflux for 4 hours. The reaction mixture was concentrated to about 20 mL, and the crystals produced were filtered and dried under high vacuum providing methyl 2,5-difluoro-3-nitrobenzoate (1.55 g, 72.4%) as a crystalline solid.

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationThe reaction mixture was concentrated to about 20 mL
  3. customthe crystals produced
  4. filtrationwere filtered
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-cfce3b7e87aa4e229623c0d6ad74f308
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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