Carbon tetrabromide → HCID 18956331、化合物

HRID 2379900ノート

反応式

HRID 2379900 の反応式
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]([CH3:18])[CH3:17].C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:20][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]([CH3:18])[CH3:17]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18956329HCID 18956329、化合物

生成物 1

HCID 18956331HCID 18956331、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Part C. A solution of the alcohol prepared in Part B above (4.18 g, 17.0 mmol) and carbon tetrabromide (6.75 g, 20.3 mmol) in methylene chloride (40 mL) was cooled to 0° C., and a solution of triphenylphosphine (5.34 g, 20.4 mmol) in methylene chloride (40 mL) was added dropwise. The mixture was stirred for 20 hours, then evaporated. The residue was separated by flash chromatography (1:2 ethyl acetate-hexane) to afford the product, 1-(5-bromopentyl)-2-(1-methylethyl)-1H-benzimidazole, as an oil (4.80 g, 15.5 mmol, 92%. 1H NMR (CDCl3): 7.79-7.72 (1H, m) ; 7.32-7.21 (3H, m); 4.14 (2H, t, J=7.5 Hz); 3.39 (2H, t, J=6.6 Hz); 3.18 (1H, heptet, J=7.0 Hz); 1.94-1.78 (4H, m); 1.63-1.50 (2H, m); 1.45 (6H, d, J=7.0 Hz).

後処理

  1. customevaporated
  2. customThe residue was separated by flash chromatography (1:2 ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-56b2f711baa6493688c9720b93ab0594
出典データセット
uspto-grants-1994_11
特許番号
US05364875

反応ノート

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