Carbon tetrabromide → 3-(Bromomethyl)-2-methoxypyridine

HRID 1972651노트

반응식

HRID 1972651 반응식
[CH3:1][O:2][C:3]1[C:8]([CH2:9]O)=[CH:7][CH:6]=[CH:5][N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>C(Cl)Cl>[Br:31][CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10630565(2-Methoxypyridin-3-yl)methanol

생성물 1

HCID 575745123-(Bromomethyl)-2-methoxypyridine수율 67.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 100-mL round-bottomed flask was added (2-methoxy-3-pyridinyl)methanol (1.12 g, 8.05 mmol), triphenylphosphine (2.32 g, 8.85 mmol, Aldrich, St. Louis, Mo.) and carbon tetrabromide (0.86 mL, 8.85 mmol, Aldrich, St. Louis, Mo.) in DCM (20 mL). The reaction mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give 3-(bromomethyl)-2-methoxypyridine (1.10 g) as a colorless oil.

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 20% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-a5944d691ad04f7299c933935d6813ce
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431563B2

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