Methyl iodide → 3-Fluoro-4-nitroanisole
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[C:12](=O)([O-])[O-].[K+].[K+].CI>CC(=O)CC>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Fluoro-4-nitrophenol (Fluorochem) (10 g, 64 mmol) was dissolved in butan-2-one (60 ml) and treated with potassium carbonate 16.6 g (120 mmol) at 40° C. for 10 minutes. The resulting suspension was cooled to 0° C., treated with methyl iodide (7.5 ml, 120 mmol), heated to 40° C. for three hours and concentrated in vacuo to 20 ml. The mixture was poured into dichloromethane (35 ml), filtered and the filtrate evaporated to give 3-fluoro-4-nitroanisole, as a white solid (8.0 g, 73%). An analytically pure sample was obtained by recrystallization from aqueous ethanol (4:1); mp 47°-49° C.; ir 1608 cm-1.
Workup
- temperatureheated to 40° C. for three hours
- concentrationconcentrated in vacuo to 20 ml
- additionThe mixture was poured into dichloromethane (35 ml)
- filtrationfiltered
- customthe filtrate evaporated
Sources & evidence
- ORD record
- ord-a74532566ea440fb9082b4fdd58f4b3d
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04906655
Reaction notes
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