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

HRID 1496931ノート

反応式

HRID 1496931 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 205577975-Bromo-2-(bromomethyl)pyrimidine収率 11%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b178772538d1467d96e8c190228d2701
出典データセット
uspto-grants-2015_12
特許番号
US09198913B2

反応ノート

読み込み中…