Sodium Carbonate → 5-Bromo-6-methoxy-isoquinoline

HRID 1436010

反応式

HRID 1436010 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[CH:6]2.[Al+3].[Cl-].[Cl-].[Cl-].[Br:17]Br.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.O>[Br:17][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 110409786-Methoxyisoquinoline

生成物 1

HCID 222265455-Bromo-6-methoxy-isoquinoline収率 34%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 6-methoxyisoquinoline (2.38 g, 14.9 mmol) in dichloromethane (55 ml) was added AlCl3 (4.4 g, 33 mmol) under nitrogen at ambient temperature. The mixture was stirred for 30 min then Br2 (0.92 ml, 18 mmol) was added at 0° C. The mixture was stirred for 2 h, then poured into water and neutralised with solid Na2CO3. The mixture was filtered through celite and the filtrate extracted with dichloromethane and chloroform. The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a residue. Flash chromatography of the residue on silica (eluent: 50-100% ethyl acetate in heptane) gave 5-bromo-6-methoxyisoquinoline (1.2 g, 34% yield).

後処理

  1. stirringThe mixture was stirred for 2 h
  2. filtrationThe mixture was filtered through celite
  3. extractionthe filtrate extracted with dichloromethane and chloroform
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give a residue

出典と根拠

ORDレコード
ord-4515ddca052643cb85f5d871328f610f
出典データセット
uspto-grants-2009_11
特許番号
US07618985B2

関連ノート

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