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

HRID 712231ノート

反応式

HRID 712231 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:28])C(=O)C1.C(Cl)Cl>C(Cl)(Cl)(Cl)Cl.CCCCCC>[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH2:8][Br:28])=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 143877445-Bromo-2-methylpyrimidine

生成物 1

HCID 205577975-Bromo-2-(bromomethyl)pyrimidine収率 25.5%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 8058Hexane溶媒

反応条件

温度
70 °C

実験手順

To an ice-cold solution of 5-bromo-2-methylpyrimidine (3.5 g, 20.23 mmol) in CCl4 (20 mL) was added AIBN (0.14 g, 2.02 mmol) followed by portion wise addition of NBS (3.6 g, 20.23 mmol) and the mixture stirred at 70° C. for 30 h. After completion of reaction (by TLC), DCM (150 mL) was added and washed with water and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 2% EtOAc:hexane to obtain the desired product (1.30 g, 25% yield). 1H NMR (CDCl3): δ 4.68 (s, 2H) and 9.03 (s, 2H).

後処理

  1. additionwas added
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified over 100-200 M silica-gel

出典と根拠

ORDレコード
ord-06da0a75b61d4a688cbd2e19bc5f5d7f
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

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