2-Phenylacetophenone → 2-Bromo-1,2-diphenylethan-1-one

HRID 1288562Notes

Reaction equation

HRID 1288562 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:16]Br>C(Cl)(Cl)Cl>[Br:16][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 99482-PhenylacetophenoneHCID 24408Bromine

Product 1

HCID 1026302-Bromo-1,2-diphenylethan-1-oneYield 72.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In chloroform (200 ml) is dissolved 2-phenylacetophenone (25.5 g) and thereto is added a solution of bromine (22 g) in chloroform (100 ml) and the mixture is stirred at room temperature for 5 hours and then allowed to stand overnight. After distilling off chloroform, to the resulting residue is added methanol. The precipitates are filtered off and the filtrate is subjected to a silica gel chromatography and eluted with chloroform. The eluates are collected and distilled to remove chloroform to give 2-bromo-2-phenylacetophenone (26 g) as an oily substance.

Workup

  1. waitto stand overnight
  2. distillationAfter distilling off chloroform
  3. additionto the resulting residue is added methanol
  4. filtrationThe precipitates are filtered off
  5. washeluted with chloroform
  6. customThe eluates are collected
  7. distillationdistilled
  8. customto remove chloroform

Sources & evidence

ORD record
ord-f4b2eea10b96457095aebe67670bd314
Source dataset
uspto-grants-1976_10
Patent number
US03988456

Reaction notes

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