N-Iodosuccinimide → 1-(5-Chloro-4-fluoro-2-hydroxy-3-iodophenyl)ethanone
Reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[I:13]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:1][C:2]1[C:3]([F:12])=[C:4]([I:13])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution of 1-(5-chloro-4-fluoro-2-hydroxyphenyl)ethanone (23.8 g, 126 mmol) in acetic acid (100 mL) was treated with N-iodosuccinimide (34.1 g, 151 mmol) and stirred at 70° C. for 2 hr. The reaction mixture was concentrated, diluted with EtOAc and quenched with sat. NaHCO3 solution until the bubbling stopped. The organic layers were separated, washed with water, dried over MgSO4 and stripped to give the desired product which was used in the next step without further purification.
Workup
- concentrationThe reaction mixture was concentrated
- additiondiluted with EtOAc
- customquenched with sat. NaHCO3 solution until the bubbling
- customThe organic layers were separated
- washwashed with water
- dry with materialdried over MgSO4
Sources & evidence
- ORD record
- ord-739c2e1325ec4b5cbca0537fbcea6110
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309251B2
Reaction notes
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