1,3-Dibromopropane → 2-(3-Bromopropoxy)-1-methoxy-3-methylbenzene

HRID 1176348Notes

Reaction equation

HRID 1176348 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].[Br:17][CH2:18][CH2:19][CH2:20]Br>C(#N)C.O>[Br:17][CH2:18][CH2:19][CH2:20][O:10][C:4]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 761732-Methoxy-6-methylphenol

Product 1

HCID 538466042-(3-Bromopropoxy)-1-methoxy-3-methylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The mixture of 2.50 g of 2-methoxy-6-methylphenol, 3.75 g of potassium carbonate and 18.3 ml of 1,3-dibromopropane in 50 ml of acetonitrile is stirred at reflux with stirring over 16 hours. The reaction mixture is cooled, diluted with 200 ml of water and extracted with tert-butyl methyl ether (2×200 ml). The organic phases are washed successively with water (200 ml) and brine (200 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.59 (1:1 EtOAc-heptane); Rt=5.10.

Workup

  1. temperatureat reflux
  2. stirringwith stirring over 16 hours
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with tert-butyl methyl ether (2×200 ml)
  5. washThe organic phases are washed successively with water (200 ml) and brine (200 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4755541843b94c59a14c9a09aa15fcda
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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