Methyl iodide → 2-Fluoro-1-methoxy-3-(trifluoromethyl)benzene
Reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:12].IC.[C:15](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[C:3]([O:12][CH3:15])=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:11])[F:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 2-fluoro-3-(trifluoromethyl)-phenol (4.87 g, 27.04 mmol) and iodomethane (4.60 g, 32.4 mmol) in acetone (50 mL) is cooled to 0° C. and then 325 mesh potassium carbonate (4.48 g, 32.4 mmol) is added. The reaction is warmed to rt and stirred for 17 hours under N2. The reaction filtered to remove the solids, and the filtrate is acidified with 1 N HCl. The mixture is diluted with water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford 4.76 g (91%) of 2-fluoro-3-methoxybenzotrifluoride that is utilized without purification. Rf=0.35 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3).
Workup
- temperatureThe reaction is warmed to rt
- filtrationThe reaction filtered
- customto remove the solids
- additionThe mixture is diluted with water
- extractionextracted with Et2O
- dry with materialThe organic layer is dried (Na2SO4)
- customthe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-c8bf09d1edef465493d84ff7d9649785
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608639B2
Reaction notes
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