Methanol → 2-Bromo-1-[1-(4-Chlorophenyl)cyclobutyl]ethanone
Reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:14](=[O:16])[CH3:15])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.CO>C(Cl)(Cl)Cl>[Br:1][CH2:15][C:14]([C:10]1([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)[CH2:13][CH2:12][CH2:11]1)=[O:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of bromine (35 ml) in chloroform (150 ml) was added dropwise over 3 hours to a stirred mixture of 1-[1-(4-chlorophenyl)cyclobutyl]ethanone (150 g), chloroform (50 ml) and methanol (235 ml). When the addition was complete, the mixture was stirred at ambient temperature for a further 3 hours, then it was diluted with ice-cold water (750 ml). The product was extracted into dichloromethane (3×200 ml), and the combined extracts were washed with saturated aqueous sodium hydrogen carbonate solution (3×100 ml) and water (100 ml), dried (MgSO4), and the solvents removed in vacuo, to leave 2-bromo-1-[1-(4-chlorophenyl)cyclobutyl]ethanone as an oil which was used without further purification.
Workup
- additionWhen the addition
- extractionThe product was extracted into dichloromethane (3×200 ml)
- washthe combined extracts were washed with saturated aqueous sodium hydrogen carbonate solution (3×100 ml) and water (100 ml)
- dry with materialdried (MgSO4)
- customthe solvents removed in vacuo
Sources & evidence
- ORD record
- ord-b13bc810fcdf4e878dd2c405288d7690
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06187802B1
Reaction notes
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