Aluminum(III) Chloride → 5'-Hydroxy-2'-iodo-4'-methoxyacetophenone

HRID 41923ノート

反応式

HRID 41923 の反応式
[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]=1

参加物

4

反応物 2

HCID 6451240Aluminum(III) ChlorideHCID 667611172'-Iodo-5'-isopropoxy-4'-methoxyacetophenone

生成物 1

HCID 667608985'-Hydroxy-2'-iodo-4'-methoxyacetophenone収率 75.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
18 °C

実験手順

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.

後処理

  1. customthen partitioned between H2O (10 mL) and additional CH2Cl2 (10 mL)
  2. extractionThe separated aqueous phase was extracted with CH2Cl2 (1×10 mL)
  3. dry with materialthe combined organic fractions were then dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washThe ensuing residue was subjected to flash chromatography (1:4 v/v ethyl acetate/hexane elution)

出典と根拠

ORDレコード
ord-b673876ef88942baad74ee5c71f316d7
出典データセット
uspto-grants-2013_09
特許番号
US08536157B2

反応ノート

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