Diethyl Ether → 1-(2-Chloro-6-fluorophenyl)ethan-1-one
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])C=1C#N.[CH3:11][Mg]Br.C([O:16][CH2:17][CH3:18])C>>[CH3:11][C:17]([C:18]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[F:10])=[O:16]Participants
4
Conditions
- Temperature
- 35 °C
Procedure
2-chloro-6-fluorobenzonitrile (42.3 g, 0.27 mol) is dissolved in anhydrous diethyl ether (170 ml) and methyl magnesium bromide (291 ml of a 2.8 M solution, 0.82 mol) is added. The whole is warmed to reflux (35° C.) overnight (16 hrs.). Then the reaction mixture is quenched in ice-water (380 ml) followed by the addition of concentrated H2SO4 (95 ml). The resultant mixture is heated to 100° C. for 3 hours and stirred overnight at room temperature. Pure product is then extracted from the mixture using chloroform (45.0 g, 95.9%).
Workup
- temperatureThe whole is warmed
- customThen the reaction mixture is quenched in ice-water (380 ml)
- additionfollowed by the addition of concentrated H2SO4 (95 ml)
- temperatureThe resultant mixture is heated to 100° C. for 3 hours
- extractionPure product is then extracted from the mixture
Sources & evidence
- ORD record
- ord-5a325dacc62c45d1ab2e87b351b4c462
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04438271
Reaction notes
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