1,5-Dibromopentane → 1-[2-[(5-Bromopentyl)oxy]ethyl]-4-(methylthio)benzene

HRID 1721906노트

반응식

HRID 1721906 반응식
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-].[Na+]>O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

참가 물질

5

반응물 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 27600862-(4-Methylsulfanylphenyl)ethanol

생성물 1

HCID 200713861-[2-[(5-Bromopentyl)oxy]ethyl]-4-(methylthio)benzene수율 76.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

4-(Methylthio)benzeneethanol (7.44 g) and 1,5 dibromopentane (30.48 g) were stirred rapidly at room temperature with TAB (1.0 g) and 12.5M aqueous sodium hydroxide (35 ml) for 64 h. The mixture was diluted with water (170 ml), extracted with ER (3×200 ml) and the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml), dried and evaporated. The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97) to give the title compound as a colourless oil (10.68 g). T.l.c. (ER-CX 1:79) Rf 0.08.

후처리

  1. extractionextracted with ER (3×200 ml)
  2. washthe combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml)
  3. customdried
  4. customevaporated
  5. customThe residual oil (29.29 g) was purified by FCC
  6. washeluting with ER-CX (0:100→3:97)

출처 및 근거

ORD 기록
ord-ba1bab03dff0470598d639f62f112036
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04853382

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