Chlorotrimethylsilane → Methyl 2,5-difluoro-3-nitrobenzoate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux for 4 hours
- concentrationThe reaction mixture was concentrated to about 20 mL
- customthe crystals produced
- filtrationwere filtered
- 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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