3-(Methylthio)-1-propanol → (3-(3-Bromo-2-methylphenoxy)propyl)(methyl)sulfane

HRID 237499

Reaction equation

HRID 237499 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:10][S:11][CH2:12][CH2:13][CH2:14]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.O>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:14][CH2:13][CH2:12][S:11][CH3:10]

Participants

7

Reactant 4

HCID 104483-(Methylthio)-1-propanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 111714303-Bromo-2-methylphenol

Product 1

HCID 86697160(3-(3-Bromo-2-methylphenoxy)propyl)(methyl)sulfane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-2-methylphenol (0.10 g), 3-(methylthio)propanol (0.055 mL), tri-n-butyl phosphine (0.12 g) and 1,1′-(azodicarbonyl)dipiperidine (0.15 g) are stirred in tetrahydrofurane for 16 hours. Water is added and the mixture extracted with diethyl ether. The organic layer is washed with brine, dried (Na2SO4) and volatiles removed under reduced pressure. The product (80 mg) is obtained after column chromatography (silica gel, n-hexane/ethyl acetate gradient 100:0 to 50:50).

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. washThe organic layer is washed with brine
  3. dry with materialdried (Na2SO4)
  4. customvolatiles removed under reduced pressure

Sources & evidence

ORD record
ord-ef70e29ed21546b2a8527d437f2c62ee
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Linked notes

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