1,3-Dibromopropane → 4-(3-Bromopropoxy)-3-methoxybenzonitrile

HRID 55595

반응식

HRID 55595 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].[Br:12][CH2:13][CH2:14][CH2:15]Br>C(#N)C>[Br:12][CH2:13][CH2:14][CH2:15][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11]

참가 물질

4

반응물 2

HCID 80011,3-DibromopropaneHCID 781354-Hydroxy-3-methoxybenzonitrile

생성물 1

HCID 104232304-(3-Bromopropoxy)-3-methoxybenzonitrile

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 4-hydroxy-3-methoxybenzonitrile (7.5 g, 50 mmol), K2O3 (12.5 g), and 1,3-dibromopropane (15 g, 75 mmol) in acetonitrile (100 ml) was heated at reflux for 3 hours and left standing at room temperature overnight. The solvent of the reaction was removed on a rotary evaporator, and the crude solid was extracted into methylene chloride (500 ml). The insolubles were filtered off. The dichloromethane solution was concentrated and the material was purified on a flash chromatography column (SiO2, 105 g; eluted with 2:3 dichloromethane:hexane, and then with dichloromethane). The desired product thus purified weighed 7.74 g (52%). Recrystallization twice from ethanol gave analytically pure 4-(3-bromopropoxy)-3-methoxybenzonitrile, m.p.=99°-101° C.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. waitleft
  4. customThe solvent of the reaction was removed on a rotary evaporator
  5. extractionthe crude solid was extracted into methylene chloride (500 ml)
  6. filtrationThe insolubles were filtered off
  7. concentrationThe dichloromethane solution was concentrated
  8. customthe material was purified on a flash chromatography column (SiO2, 105 g
  9. washeluted with 2:3 dichloromethane
  10. customThe desired product thus purified
  11. customRecrystallization twice from ethanol

출처 및 근거

ORD 기록
ord-07747248041f48f7a6a6b7d4f1cc431d
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624927

연결된 노트

불러오는 중…