Water → HCID 57435890, 화합물

HRID 30581노트

반응식

HRID 30581 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]O)[CH:5]=[CH:6][CH:7]=1.C(N(S(F)(F)[F:20])CC)C.O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][F:20])[CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 57435887931430-20-5

생성물 1

HCID 57435890HCID 57435890, 화합물수율 63%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 5-(3-bromophenyl)pentan-1-ol (0.63 g, 2.6 mmol) in methylene chloride at −78° C. was treated with a solution of diethylamino sulfur trifluoride (DAST) (0.7 mL, 5.2 mmol) in methylene chloride, allowed to warm to room temperature, stirred for 0.5 h at room temperature, poured into water and extracted with ether. The extracts were combined washed sequentially with saturated sodium bicarbonate and water, dried over magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by flash chromatography on silica gel, 40:1 hexane/ethyl acetate as eluent to give 1-bromo-3-(5-fluoropentyl)benzene as a pale yellow oil, 0.4 g (63% yield); 1H NMR (DMSO-d6) δ 1.3 (m, 2H); 1.6 (m, 4H); 2.5 (t, 2 H); 4.4 (dxt, 2H); 7.2 (m, 2 H); 7.4 (m, 2 H); MS [(+)ESI] m/z=245 [M−H]+.

후처리

  1. extractionextracted with ether
  2. washThe extracts were combined washed sequentially with saturated sodium bicarbonate and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by flash chromatography on silica gel, 40:1 hexane/ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-edecd3fd90264d50b6719419c29acc58
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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