Bromine → HCID 19375988, compound

HRID 2211153Notes

Reaction equation

HRID 2211153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].[Br:15]Br.C(=O)(O)[O-].[K+]>C(Cl)(Cl)Cl>[Br:15][CH2:13][C:12]([C:4]1[CH:5]=[C:6]([O:10][CH3:11])[C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=1)=[O:14]

Participants

5

Reactant 3

HCID 24408BromineHCID 516893Potassium BicarbonateHCID 21192648HCID 21192648, compound

Product 1

HCID 19375988HCID 19375988, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1-(3-Chloro-4,5-dimethoxyphenyl)-ethanone (31.6 g) was dissolved in chloroform (140 ml) and the solution was stirred at room temperature and treated dropwise with a solution of bromine (7.9 ml) in chloroform (60 ml). After a further 45 min the mixture was neutralised with aqueous potassium bicarbonate solution. The organic layer was separated and washed with sodium chloride solution, dried over sodium sulphate, then filtered and evaporated to dryness. The resultant oil (42.8 g) was crystallized from ether-hexane to give 2-bromo-1-(3-chloro-4,5-dimethoxyphenyl)-ethanone (32.0 g), m.p. 76.5°-78° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resultant oil (42.8 g) was crystallized from ether-hexane

Sources & evidence

ORD record
ord-5b01613b08dd476b8d9fcb312a66edd5
Source dataset
uspto-grants-1995_10
Patent number
US05462959

Reaction notes

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