Bromine → HCID 19031562, compound

HRID 266870Notes

Reaction equation

HRID 266870 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2([C:14](=[O:16])[CH3:15])[CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1>ClCCl.CO>[Br:1][CH2:15][C:14]([C:10]1([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=2)[CH2:13][CH2:12][CH2:11]1)=[O:16]

Participants

5

Reactant 2

HCID 24408BromineHCID 19031557HCID 19031557, compound

Product 1

HCID 19031562HCID 19031562, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (9.9 ml) in dichloromethane (50 ml) was added dropwise at 10°-15° C. over 3 hours to a stirred solution of 1-[1-(3-chlorophenyl)cyclobutyl]-ethanone (38 g) in a mixture of methanol (75 ml) and dichloromethane (15 ml). When the addition was complete, the mixture was stirred at ambient temperature for 2.5 hours, then poured onto an excess of ice-water. The aqueous layer was separated and the product extracted into dichloromethane (3×90 ml). The combined organic solutions were washed with saturated aqueous sodium hydrogen carbonate solution (2×100 ml) and water (100 ml), dried over calcium chloride and the solvent removed in vacuo to leave 2-bromo-1-[1-(3-chlorophenyl)cyclobutyl]ethanone as an oil (47 g).

Workup

  1. additionWhen the addition
  2. customThe aqueous layer was separated
  3. extractionthe product extracted into dichloromethane (3×90 ml)
  4. washThe combined organic solutions were washed with saturated aqueous sodium hydrogen carbonate solution (2×100 ml) and water (100 ml)
  5. dry with materialdried over calcium chloride
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-12b6021a80c940b28d1af0774f2485c7
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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