Hydrogen Bromide → 2-Bromo-6-chloro-1-indanone

HRID 46628

Reaction equation

HRID 46628 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1.Br>C(OC(=O)C)C>[Br:1][CH:9]1[CH2:8][C:7]2[C:11](=[CH:12][C:4]([Cl:3])=[CH:5][CH:6]=2)[C:10]1=[O:13]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 51007056-Chloro-1-indanone

Product 1

HCID 122065232-Bromo-6-chloro-1-indanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 9.59 g (60.0 mmoles) of bromine in 20 ml of acetic acid ethyl ester is added dropwise to a solution of 10.0 g (60.0 mmoles) of 6-chloro-1-indanone in 80 ml of acetic acid ethyl ester and 0.5 ml of 48% strength aqueous hydrobromic acid. After stirring for 3 hours, the reaction solution is concentrated to dryness, the residue is stirred with 50 ml of water and the precipitate is filtered off. The crude product of melting point 84°-87° is recrystallized from petroleum ether 60/70 and gives the pure product of melting point 92°-94° C.

Workup

  1. concentrationthe reaction solution is concentrated to dryness
  2. stirringthe residue is stirred with 50 ml of water
  3. filtrationthe precipitate is filtered off
  4. customThe crude product of melting point 84°-87° is recrystallized from petroleum ether 60/70
  5. customgives the pure product of melting point 92°-94° C.

Sources & evidence

ORD record
ord-840378d0473244f485c09bd95c4d779f
Source dataset
uspto-grants-1979_11
Patent number
US04174397

Linked notes

Loading…