Benzonitrile → 2-(3-Bromo-phenyl)-1-phenyl-ethylamine
Reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][Mg]Br.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Br:9][C:10]1[CH:11]=[C:12]([CH2:13][CH:1]([NH2:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:17][CH:18]=1Participants
Procedure
Benzonitrile (500 mg, 4.849 mmol) was added dropwise to a solution of 3-bromobenzylmagnesium bromide (0.275 M solution in diethyl ether, 21.1 ml, 5.818 mmol) under an atmosphere of nitrogen at room temperature. The reaction mixture was then heated to reflux for a period of 2 hours then allowed to cool. Lithium aluminium hydride (1.0 M in THF, 4.85 ml, 4.849 mmol) was then added cautiously and the reaction mixture was allowed to heat at reflux for a further 16 hours. Upon cooling, the reaction was quenched by cautious and dropwise addition of water (5 ml) and then partitioned between water (20 ml) and ethyl acetate (100 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. Purification by ion exchange chromatography afforded the desired compound (420 mg, 31%).
Workup
- temperatureThe reaction mixture was then heated
- temperatureto reflux for a period of 2 hours
- temperatureto cool
- temperatureto heat
- temperatureat reflux for a further 16 hours
- temperatureUpon cooling
- customthe reaction was quenched by cautious and
- additiondropwise addition of water (5 ml)
- custompartitioned between water (20 ml) and ethyl acetate (100 ml)
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customPurification by ion exchange chromatography
Sources & evidence
- ORD record
- ord-8718f95e3041493790a5e359dad8a6e1
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247576B2
Reaction notes
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