Bromine → 2-Bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethan-1-one
Reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([C:15](=[O:17])[CH3:16])[CH2:14][CH2:13][CH2:12]2)[CH:7]=[CH:8][C:9]=1[Cl:10]>C(Cl)(Cl)Cl.CO>[Br:1][CH2:16][C:15]([C:11]1([C:6]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=2)[CH2:14][CH2:13][CH2:12]1)=[O:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of bromine (96 ml) in chloroform (427 ml) was added dropwise at 10°-15° C. over 1.5 hours to a stirred solution of 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone (477.2 g; prepared in a similar manner to that described above) in a mixture of methanol (643 ml) and chloroform (107 ml). After the addition was complete, the mixture was stirred at ambient temperature for 3 hours, then poured into ice-water (21). The aqueous layer was separated and washed with dichloromethane (3×500 ml), then the combined organic solutions were washed with saturated aqueous sodium hydrogencarbonate solution (2×400 ml) and water (500 ml), dried over calcium chloride, and the, solvents were removed in vacuo to leave 2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone as an orange oil (593.5 g) which was used without purification.
Workup
- customprepared in a similar manner to that
- additionAfter the addition
- customThe aqueous layer was separated
- washwashed with dichloromethane (3×500 ml)
- washthe combined organic solutions were washed with saturated aqueous sodium hydrogencarbonate solution (2×400 ml) and water (500 ml)
- dry with materialdried over calcium chloride
- customthe, solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-ff9a3dbf0061487f80f46ab5857f1288
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05652271
Reaction notes
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