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 (18 ml) in chloroform (80 ml) was added dropwise at 10°-15° C. over 1.5 hours to a stirred solution of the above 1-[1-(3,4-dichlorophenyl)-cyclobutyl]ethanone (89.6 g) in a mixture of methanol (120 ml) and chloroform (20 ml). When the addition was complete, the mixture was stirred at ambient temperature for 1 hour, then poured onto an excess of ice-water. The aqueous layer was separated and the product extracted into dichloromethane (2×150 ml). The combined organic solutions were washed with saturated aqueous sodium hydrogen carbonate solution (2×200 ml) then with water, dried over calcium chloride and the solvent removed in vacuo to yield an oil. The oil was distilled to give 2-bromo-l-[1-(3,4-dichlorophenyl)-cyclobutyl]ethanone (88.31 g), b.p. 148°-154° C./0.66 mbar.
Workup
- additionWhen the addition
- customThe aqueous layer was separated
- extractionthe product extracted into dichloromethane (2×150 ml)
- washThe combined organic solutions were washed with saturated aqueous sodium hydrogen carbonate solution (2×200 ml)
- dry with materialwith water, dried over calcium chloride
- customthe solvent removed in vacuo
- customto yield an oil
- distillationThe oil was distilled
Sources & evidence
- ORD record
- ord-8a7d85cdad364527ad469952f7984b55
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05652271
Reaction notes
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