Carbon Tetrachloride → Pyridine, 2-(bromomethyl)-5-(2,2,2-trifluoroethoxy)-

HRID 911300

반응식

HRID 911300 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=1.C1C(=O)N([Br:21])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Br:21][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([F:11])([F:13])[F:12])=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl Peroxide2회HCID 67184N-bromobutanimide2회HCID 235684332-Methyl-5-(2,2,2-trifluoroethoxy)pyridine

생성물 1

HCID 57655951Pyridine, 2-(bromomethyl)-5-(2,2,2-trifluoroethoxy)-수율 13%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

Add 2-methyl-5-(2,2,2-trifluoroethoxy)-pyridine (2.5 g, 13.1 mmol), NBS (2.3 g, 13.1 mmol) and benzoyl peroxide (50 mg) to a flask containing carbon tetrachloride (30 mL). Heat the mixture at 80° C. in a sealed flask for 16 h. Cool the flask, add NBS (1.1 g, 6.5 mmol) and benzoyl peroxide (100 mg), then continue heating at 80° C. for an additional 5 h. Cool the mixture, dilute with DCM, then wash with saturated sodium bisulfite (10 mL). Collect the organic layer and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to obtain the desired intermediate (460 mg, 13%).

후처리

  1. temperatureCool the flask
  2. temperaturecontinue heating at 80° C. for an additional 5 h
  3. temperatureCool the mixture
  4. washwash with saturated sodium bisulfite (10 mL)
  5. customCollect the organic layer
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

출처 및 근거

ORD 기록
ord-e1def4c742d748bc8e65026f28389864
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

연결된 노트

불러오는 중…