Acetophenone → 2-Chloroacetophenone
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].I([Cl:13])(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl>[Cl:13][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of acetophenone (5.00 g, 41.6 mmol) in DCM (42 ml), was added benzyltrimethylammonium tetrachloroiodate (28.8 g, 83.0 mmol). The reaction was heated at 60° C. for 1 hour, then the solvent was evaporated under vacuum. The residue was portioned between DCM (300 ml) and water (300 ml). The organic phase was washed sequentially with aqueous Na2S2O5 and brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was triturated with petroleum ether to obtain 2-chloro-1-phenylethanone (4.90 g, 76.2% yield).
Workup
- customthe solvent was evaporated under vacuum
- washThe organic phase was washed sequentially with aqueous Na2S2O5 and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated to dryness
- customThe residue was triturated with petroleum ether
Sources & evidence
- ORD record
- ord-955b8d9b4cba4911a28ebc2f2db0b8e8
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492548B2
Reaction notes
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