Bromine → 2-Bromo-4-n-hexyl-1-methoxybenzene

HRID 1721432Notes

Reaction equation

HRID 1721432 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:15]Br.S([O-])([O-])=O.[Na+].[Na+]>CO>[Br:15][C:11]1[CH:12]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:8]=[CH:9][C:10]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 5785994-Hexylanisole

Product 1

HCID 224149182-Bromo-4-n-hexyl-1-methoxybenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

26.4 g (0.137 mol) of 4-n-hexyl-1-methoxybenzene was dissolved in 200 ml of methanol. 26.4 g (0.156 mol) of bromine was added while stirring under cooling with ice. The mixture was stirred for 2 hours, while raising the temperature to room temperature. Sodium sulfite was added to the reaction mixture to decompose an excess amount of bromine, whereupon the mixture was extracted with chloroform-water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified by column chromatography (silica gel, 20:1 mixture of n-hexane and ethyl acetate) to obtain 35.18 g (yield, 95.8%) of a colorless oil of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was stirred for 2 hours
  3. extractionwhereupon the mixture was extracted with chloroform-water
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by column chromatography (silica gel, 20:1 mixture of n-hexane and ethyl acetate)
  9. customto obtain

Sources & evidence

ORD record
ord-d9c6b350df924772831331b0c086fc2a
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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