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

HRID 1436010

반응식

HRID 1436010 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 222265455-Bromo-6-methoxy-isoquinoline수율 34%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4515ddca052643cb85f5d871328f610f
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618985B2

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