Methanol → 1-Fluoro-2-(methoxymethyl)-4-nitrobenzene
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[F:12].[CH3:13][OH:14]>[Ag-]=O>[F:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][O:14][CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 54 °C
Procedure
Under argon, 250 g (1.07 mol) of 2-(bromomethyl)-1-fluoro-4-nitrobenzene were introduced as initial charge in 2.5 l of methanol, 371 g (1.60 mol) of silver(I) oxide were added and the mixture was stirred for 2.5 h at 52-56° C. After cooling to RT, suction filtration over kieselguhr was carried out, followed by after-washing with methanol, and the solvent was removed on a rotary evaporator. The crude product was purified by distillation on a short-path evaporator at a jacket temperature of 104° C. and 0.56 mbar. This gave 184.5 g (93%) of the desired product.
Workup
- temperatureAfter cooling to RT
- filtrationsuction filtration over kieselguhr
- washby after-washing with methanol
- customthe solvent was removed on a rotary evaporator
- distillationThe crude product was purified by distillation on a short-path evaporator at a jacket temperature of 104° C. and 0.56 mbar
Sources & evidence
- ORD record
- ord-31882c025de8413fbe830b83a83dfcd1
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802860B2
Reaction notes
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