Azobisisobutyronitrile → 5-Bromo-2-(bromomethyl)pyrimidine

HRID 1496931노트

반응식

HRID 1496931 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.[Br:9]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH2:8][Br:9])=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 143877445-Bromo-2-methylpyrimidine

생성물 1

HCID 205577975-Bromo-2-(bromomethyl)pyrimidine수율 11%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

반응 조건

온도
60 °C

실험 절차

A mixture of 5-bromo-2-methylpyrimidine (119) (1.34 g, 7.75 mmol), N-bromosuccinimide (1.40 g, 7.87 mmol) and AIBN (0.13 g, 0.79 mmol) in CCl4 (15 mL) was stirred at 60° C. for 3 h. The resulting mixture was filtered, the filter cake was washed with Et2O (100 mL), and the combined filtrates were concentrated under reduced pressure. Column chromatography of the residue, eluting with 2:1 EtOAc:hexanes, gave 5-bromo-2-(bromomethyl)pyrimidine (120) (0.214 g, 11%) as a white solid: mp 55-57° C.; 1H NMR (CDCl3) δ 8.79 (s, 2H), 4.57 (s, 2H). Anal. (C5H4Br2N2) C, H, N.

후처리

  1. filtrationThe resulting mixture was filtered
  2. washthe filter cake was washed with Et2O (100 mL)
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. washColumn chromatography of the residue, eluting with 2:1 EtOAc

출처 및 근거

ORD 기록
ord-b178772538d1467d96e8c190228d2701
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198913B2

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