Sulfuric Acid → 5-Bromo-8-fluoroisoquinoline

HRID 272778노트

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HRID 272778 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([CH:15]=1)[CH:7]=[N:8][CH2:9][CH:10](OC)OC.S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]2[C:15]=1[CH:10]=[CH:9][N:8]=[CH:7]2

참가 물질

3

반응물 2

HCID 1118Sulfuric Acid2회HCID 692158965-Bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine

생성물 1

HCID 687560095-Bromo-8-fluoroisoquinoline수율 2%

반응 조건

온도
135 °C

실험 절차

A mixture of 5-bromo-2-fluorobenzaldehyde (15 g, 74 mmol) and 2,2-dimethoxy-ethylamine (7.77 g, 74 mmol) in toluene (142 mL) was heated to reflux for 30 minutes using a Dean-Stark trap to remove water. The solution was then concentrated under vacuum to provide 5-bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine. 5-Bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine and cold concentrated sulfuric acid (28 mL) were added separately, dropwise, over a period of 20 minutes to concentrated sulfuric acid (83 mL) at 140° C. The mixture was stirred at 135° C. for 30 minutes, allowed to cool, and carefully poured onto ice. Filtered to remove solids and the mixture was washed with dichloromethane. The aqueous layer was made basic by cautious addition of 50% sodium hydroxide solution, and extracted with diethyl ether. Combined ether layers were dried (MgSO4), filtered and concentrated under vacuum to provide 310 mg (2%) of the desired product. MS (ESI) m/e 226 (M+H)+.

후처리

  1. temperatureto cool
  2. additioncarefully poured onto ice
  3. filtrationFiltered
  4. customto remove solids
  5. washthe mixture was washed with dichloromethane
  6. additionThe aqueous layer was made basic by cautious addition of 50% sodium hydroxide solution
  7. extractionextracted with diethyl ether
  8. dry with materialCombined ether layers were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-4a4735bab34b4fb89d8dfd701f9b5e23
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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