3-Fluoroanisole → HCID 22475212, compound
Reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[F:15][C:16]1[CH:17]=[C:18]([O:22][CH3:23])[CH:19]=[CH:20][CH:21]=1>[N+](C1C=CC=CC=1)([O-])=O>[F:15][C:16]1[CH:17]=[C:18]([O:22][CH3:23])[CH:19]=[CH:20][C:21]=1[C:10]([C:9]1[CH:13]=[CH:14][C:6]([F:5])=[CH:7][CH:8]=1)=[O:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a cold (5° C.) mixture of aluminium trichloride (144 g, 1.08 mol, 1.13 eq.) in nitrobenzene (450 mL) was slowly added a solution of 4-fluorobenzoyl chloride (120 mL, 1 mol, 1.05 eq.) in nitrobenzene (200 mL). 3-fluoroanisole (108.5 mL, 0.95 mol) was slowly added to the reaction mixture. The cooling bath was removed and the reaction mixture was stirred 3 h at 20° C., and poured into ice-water. The aqueous layer was extracted with dichloromethane (2 times). The combined organic layers were dried over sodium sulfate, filtered and the volatiles were removed in vacuo. The crude mixture was crystallized in cyclohexane, filtered and the solid was washed with cyclohexane. The solid was dried in vacuo, affording the title compound (57.78 g, 25%) as a white solid.
Workup
- customThe cooling bath was removed
- additionpoured into ice-water
- extractionThe aqueous layer was extracted with dichloromethane (2 times)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- customthe volatiles were removed in vacuo
- customThe crude mixture was crystallized in cyclohexane
- filtrationfiltered
- washthe solid was washed with cyclohexane
- customThe solid was dried in vacuo
Sources & evidence
- ORD record
- ord-cc0452c032674dd5a4c502ee0f47248a
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576088B2
Reaction notes
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