Aluminum(III) Chloride → 5'-Hydroxy-2'-iodo-4'-methoxyacetophenone
Reaction equation
[I:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10]C(C)C)=[CH:4][C:3]=1[C:14](=[O:16])[CH3:15].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[OH:10][C:5]1[C:6]([O:8][CH3:9])=[CH:7][C:2]([I:1])=[C:3]([C:14](=[O:16])[CH3:15])[CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 18 °C
Procedure
A solution of ketone 9 (625 mg, 1.87 mmol) in dry CH2Cl2 (5 mL), was treated with AlCl3 (325 mg, 2.44 mmol) and the resulting mixture stirred at 18° C. under a nitrogen atmosphere for 21 h then partitioned between H2O (10 mL) and additional CH2Cl2 (10 mL). The separated aqueous phase was extracted with CH2Cl2 (1×10 mL) and the combined organic fractions were then dried (MgSO4), filtered and concentrated under reduced pressure. The ensuing residue was subjected to flash chromatography (1:4 v/v ethyl acetate/hexane elution) to afford the title compound 13 (411 mg, 75%) as a pale-yellow solid, m.p. 109.4-110.6° C., Rf 0.5 in 1:1 v/v ethyl acetate/hexane.
Workup
- customthen partitioned between H2O (10 mL) and additional CH2Cl2 (10 mL)
- extractionThe separated aqueous phase was extracted with CH2Cl2 (1×10 mL)
- dry with materialthe combined organic fractions were then dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- washThe ensuing residue was subjected to flash chromatography (1:4 v/v ethyl acetate/hexane elution)
Sources & evidence
- ORD record
- ord-b673876ef88942baad74ee5c71f316d7
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536157B2
Reaction notes
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