Bromine → 2-Bromo-1-[1-(2-naphthyl)cyclobutyl]ethanone

HRID 266868Notes

Reaction equation

HRID 266868 reaction equation
[Br:1]Br.[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13]1([C:17](=[O:19])[CH3:18])[CH2:16][CH2:15][CH2:14]1>C(Cl)(Cl)Cl.CO>[Br:1][CH2:18][C:17]([C:13]1([C:4]2[CH:5]=[CH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:3]=2)[CH2:16][CH2:15][CH2:14]1)=[O:19]

Participants

5

Reactant 2

HCID 24408BromineHCID 21258447HCID 21258447, compound

Product 1

HCID 212584952-Bromo-1-[1-(2-naphthyl)cyclobutyl]ethanone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of bromine (4.3 ml) in chloroform (20 ml) was added dropwise over 30 minutes at 10°-15° C. to a stirred solution of 1-[1-(2-naphthyl)cyclobutyl]-ethanone (20 g) in a mixture of methanol (20 ml) and chloroform (30 ml). The mixture was then stirred at ambient temperature for 1.5 hours, poured onto ice-water (300 ml) and the product extracted into dichloromethane (3×150 ml). The extracts were washed with saturated aqueous sodium hydrogen carbonate solution, then water, dried over calcium chloride and the solvent removed in vacuo to give 2-bromo-1-[1-(2-naphthyl)cyclobutyl]-ethanone as an oil (24.0 g).

Workup

  1. additionpoured onto ice-water (300 ml)
  2. extractionthe product extracted into dichloromethane (3×150 ml)
  3. washThe extracts were washed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialwater, dried over calcium chloride
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f93d5d070a3b465e9a77513f2f87ddd5
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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