Methanol → Methyl 2-fluoro-5-methoxy-4-nitrobenzoate
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9](F)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:26][OH:27]>C1COCC1>[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([O:27][CH3:26])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl 2,5-difluoro-4-nitrobenzoate (Apollo, 500 mg; 2.30 mmol; 1 eq.) was dissolved in MeOH (10 mL). The solution was cooled down to 0° C. Lithium bis(trimethylsilyl)amide (2.30 mL; 1 M; 2.30 mmol; 1 eq.) was added as solution in THF. After addition, the reaction mixture was stirred at RT overnight. Solvents were evaporated and the crude mixture was dissolved in EtOAc, washed with water, brine and dried over MgSO4. The resulting crude product was purified by flash chromatography (c-hex/EtOAc 90:10), affording the title product as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 7.60-7.52 (m, 2H), 3.93 (s, 3H), 3.91 (s, 3H). HPLC (Method A) Rt 3.88 min (Purity: 88.6%).
Workup
- additionAfter addition
- customSolvents were evaporated
- dissolutionthe crude mixture was dissolved in EtOAc
- washwashed with water, brine
- dry with materialdried over MgSO4
- customThe resulting crude product was purified by flash chromatography (c-hex/EtOAc 90:10)
Sources & evidence
- ORD record
- ord-5d9cb3e83eeb4177bf8e89e7bfeb51e4
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
Loading…