3-(Methylthio)-1-propanol → 2-Bromo-1,3-dimethyl-5-[3-(methylthio)propoxy]benzene

HRID 15660

Reaction equation

HRID 15660 reaction equation
[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]

Participants

7

Reactant 4

HCID 104483-(Methylthio)-1-propanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 819704-Bromo-3,5-dimethylphenol

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d925f96ad2644afc88152e75846ea9ee
Source dataset
uspto-grants-2010_06
Patent number
US07732626B2

Linked notes

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