Aluminum(III) Chloride → 6-Bromoisoquinoline

HRID 1621282

反応式

HRID 1621282 の反応式
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:29]=[CH:28][C:9]([CH2:10][N:11]([CH2:22][CH:23](OC)OC)S(C2C=CC(C)=CC=2)(=O)=O)=[CH:8][CH:7]=1>ClCCl>[Br:5][C:6]1[CH:29]=[C:28]2[C:9](=[CH:8][CH:7]=1)[CH:10]=[N:11][CH:22]=[CH:23]2

参加物

4

反応物 2

HCID 6451240Aluminum(III) ChlorideHCID 59226245N-(4-Bromo-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzenesulfonamide

生成物 1

HCID 3136816-Bromoisoquinoline収率 60.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mechanically stirred suspension of 95.2 g (699.5 mmol) AlCl3 in 400 ml dichloromethane a solution of 59.9 g (139.8 mmol) N-(4-Bromo-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzenesulfonamide (2) in 400 ml dichloromethane was added and the reaction was stirred at room temperature for 4 h. After standing overnight, the reaction mixture was poured on ice, the organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane solutions were washed with 1 N NaOH (2×) and saturated NaHCO3-solution (2×). After drying with MgSO4 and evaporation of the solvent, the crude product was purified by silicagel chromatography (heptane/ethyl acetate 1:1) to yield 17.5 g of the title compound. Rt=0.68 min (Method C). Detected mass: 208.1/210.1 (M+H+).

後処理

  1. additionwas added
  2. waitAfter standing overnight
  3. additionthe reaction mixture was poured on ice
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with dichloromethane
  6. washThe combined dichloromethane solutions were washed with 1 N NaOH (2×) and saturated NaHCO3-solution (2×)
  7. dry with materialAfter drying with MgSO4 and evaporation of the solvent
  8. customthe crude product was purified by silicagel chromatography (heptane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-f82307a1177c49c1a1c5d49ca0815f86
出典データセット
uspto-grants-2014_07
特許番号
US08772492B2

関連ノート

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