Hydrogen Bromide → Phenacyl bromide

HRID 1474635Notes

Reaction equation

HRID 1474635 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BrH:10].BrBr.CC(O)=O>CC(O)=O.C(OC(=O)C)C>[Br:10][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 7410AcetophenoneHCID 87433071bromine AcOH

Product 1

HCID 6259Phenacyl bromideYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of acetophenone (500 mg, 4.16 mmol) in AcOH (20 mL) and catalytic amount of aq. HBr, 10% Br2/AcOH (2.12 mL) was added at 0° C. The reaction mixture was stirred for 2 h at r.t. After completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethylacetate (100 mL) and washed with water (20 mL) and brine (20 mL) successively. The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 1:9 EtOAc:hexane) to afford the title compound (825 mg, 4.1 mmol, 100%).

Workup

  1. customAfter completion of the reaction
  2. washwashed with water (20 mL) and brine (20 mL) successively
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe volatiles were evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 1:9 EtOAc:hexane)

Sources & evidence

ORD record
ord-8571d9d7a8624796a626596070d1d05f
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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