Hydrogen Bromide → HCID 18941092, compound

HRID 1076118Notes

Reaction equation

HRID 1076118 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[CH2:4][CH2:3]1.C(Cl)(Cl)Cl.[BrH:17]>C(OCC)(=O)C>[Br:17][CH:4]1[CH2:3][CH:2]([CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:12]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 6212ChloroformHCID 892321,2,3,4-Tetrahydro-4-methylnaphthalen-1-one

Product 1

HCID 18941092HCID 18941092, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Commercially available 4-methyl-1-tetralone, 32.0 grams, contained in 250 ml. of chloroform and 50 ml. of ethyl acetate is heated to boiling. A mixture of 98.3 grams of cupric bromide and 50 ml. of ethyl acetate is heated to its reflux temperature. After all of the hydrogen bromide is evolved, the mixture is maintained at its reflux temperature for an additional hour. The reaction mixture is filtered while hot, the residue washed with boiling chloroform and the combined filtrates evaporated to dryness in vacuo. The residue is dissolved in a minimum of methylene chloride, placed upon an alumina column and eluted with methylene chloride. The eluate is concentrated and the desired 2-bromo-4-methyl-1-tetralone obtained as a dark oil.

Workup

  1. temperaturereflux temperature
  2. temperaturethe mixture is maintained at its
  3. temperaturereflux temperature for an additional hour
  4. filtrationThe reaction mixture is filtered while hot, the residue
  5. washwashed with boiling chloroform
  6. customthe combined filtrates evaporated to dryness in vacuo
  7. dissolutionThe residue is dissolved in a minimum of methylene chloride
  8. washeluted with methylene chloride
  9. concentrationThe eluate is concentrated

Sources & evidence

ORD record
ord-3f20b1c0c8744fae90252fef2d03d760
Source dataset
uspto-grants-1976_05
Patent number
US03954983

Reaction notes

Loading…