3-甲硫基丙醇 → 2-Bromo-1,3-dimethyl-5-[3-(methylthio)propoxy]benzene

HRID 1908905笔记

反应方程式

HRID 1908905 反应方程式
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[CH3:11][S:12][CH2:13][CH2:14][CH2:15]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:15][CH2:14][CH2:13][S:12][CH3:11])=[CH:4][C:3]=1[CH3:10]

参与物

7

反应物 4

HCID 104483-甲硫基丙醇HCID 13831三丁基膦HCID 73042偶氮二甲酰二哌啶HCID 819704-溴-3,5-二甲酚

产物 1

HCID 593425752-Bromo-1,3-dimethyl-5-[3-(methylthio)propoxy]benzene收率 87%

试剂、催化剂与溶剂 2

HCID 1140甲苯溶剂HCID 8058正己烷溶剂

实验过程

To a solution of 4-bromo-3,5-dimethylphenol (4.02 g, 20.0 mmol), 3-(methylthio)-1-propanol (2.12 g, 20.0 mmol) and tributylphosphine (7.97 mL, 32.0 mmol) in toluene (320 mL) was added 1,1′-(azodicarbonyl)dipiperidine (8.07 g, 32.0 mmol), and the mixture was stirred at room temperature for 18 hr under nitrogen atmosphere. Hexane (160 mL) was added to the reaction mixture, the insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75) to give the title compound (5.03 g, yield 87%) as a pale-yellow oil.

后处理

  1. filtrationthe insoluble substance was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75)

来源与证据

ORD记录
ord-e340654a9ac04344b2995fe6418edb08
来源数据集
uspto-grants-2013_12
专利号
US08598226B2

反应笔记

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