Carbon tetrabromide → HCID 18956331, 화합물

HRID 2379900노트

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HRID 2379900 반응식
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]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18956329HCID 18956329, 화합물

생성물 1

HCID 18956331HCID 18956331, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-56b2f711baa6493688c9720b93ab0594
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05364875

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