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]>C1(C)C=CC=CC=1.[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
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
30 g (128 mmol) of the compound from Example 26A are dissolved in 1.3 l of anhydrous toluene, and 45 g (192 mmol) of silver(I) oxide and 24.6 g (769 mmol) of anhydrous methanol are added. The mixture is heated at 60° C. for 16 h. The mixture is then allowed to cool and filtered through silica gel. The product is eluted fractionally using a gradient of cyclohexane and cyclohexane/ethyl acetate 25:1. The product fractions are evaporated to dryness under reduced pressure and dried under reduced pressure. This gives 17 g (72% of theory) of the desired product.
Workup
- temperatureto cool
- filtrationfiltered through silica gel
- washThe product is eluted fractionally
- customThe product fractions are evaporated to dryness under reduced pressure
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-6ef849e9721c4a8c83c7e81cc6e2ba03
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846934B2
Reaction notes
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