Hydrogen Bromide → 1-(Bromomethyl)-4-ethylbenzene
Reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1)[CH3:2].[BrH:11]>>[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Br:11])=[CH:5][CH:4]=1)[CH3:2]Participants
Procedure
A mixture of 2.72 g (20.0 mmol) of 4-ethylbenzyl alcohol (purchased from Aldrich) and 50 ml of 47% hydrobromic acid (purchased from Wako Junyaku Kogyo) was stirred at room temperature for 30 minutes vigorously and extracted with hexane to give 3.98 g of 4-ethylbenzyl bromide as a colorless oil. Subsequently, to 20 ml of 1.96 g (40.0 mmol) of sodium cyanide (purchased from Kokusan Kagaku) in dimethyl sulfoxide (purchased from Aldrich) solution heated at 50° C. was added 3.98 g of the above 4-ethylbenzyl bromide, the mixture was stirred at ambient temperature for 3 hours, the resultant reaction mass was dissolved in water and extracted with hexane, and hexane was removed to give 2.70 g (yield: 93.1%) of 4-ethylphenylacetonitrile as a light yellow oil.
Workup
- extractionextracted with hexane
Sources & evidence
- ORD record
- ord-a9420ff1fce5432c83509cfd42825d4e
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05574062
Reaction notes
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