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

HRID 635349Notes

Reaction equation

HRID 635349 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>CCOCC>[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

4

Reactant 2

HCID 24408Bromine2×HCID 21258447HCID 21258447, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Bromine (2.6 ml) was added dropwise over 1 hour at ambient temperature to a stirred solution of 1-[1-(2-naphthyl)cyclobutyl]ethanone (11.25 g) in ether (300 ml). After the addition was complete and the bromine colour had dissipated, the mixture was stirred at ambient temperature for a further 0.5 hour then it was washed with water (100 ml), saturated aqueous sodium hydrogen carbonate solution (2×100 ml) and water (100 ml), dried (MgSO4), and the solvent removed in vacuo to give 2-bromo-1-[1-(2-naphthyl)cyclobutyl]ethanone as an oil which was used without purification.

Workup

  1. additionAfter the addition
  2. washit was washed with water (100 ml), saturated aqueous sodium hydrogen carbonate solution (2×100 ml) and water (100 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ad9b9affb4a34826957a2cad043f3c1e
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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