Hydrogen Bromide → 2-Bromo-1-(1-naphthalenyl)ethanone

HRID 26539

Reaction equation

HRID 26539 reaction equation
[C:1]1([C:11]([CH3:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[BrH:18]>[Cu](Br)Br.C(OCC)(=O)C>[C:1]1([C:11]([CH2:13][Br:18])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 6212ChloroformHCID 136631-Acetylnaphthalene

Product 1

HCID 38305132-Bromo-1-(1-naphthalenyl)ethanone

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 1-naphthyl ketone (10.1 g.), in 50 ml of a 1:1 mixture of chloroform and ethyl acetate is treated with 26.5 g. of copper (II) bromide. The resulting reaction mixture is heated under reflux with vigorous stirring until the evolution of hydrogen bromide ceases. When the reaction is complete the solvent is removed, ether is added and the copper (I) bromide is removed by filtration. Evaporation of the filtrate under reduced pressure yields crude bromomethyl 1-naphthyl ketone.

Workup

  1. additionis treated with 26.5 g
  2. customThe resulting reaction mixture
  3. temperatureis heated
  4. temperatureunder reflux
  5. customis removed
  6. additionether is added
  7. customthe copper (I) bromide is removed by filtration
  8. customEvaporation of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-1489e7152d2f4faab50106df544efc62
Source dataset
uspto-grants-1979_04
Patent number
US04150153

Linked notes

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