Dimethyl Sulfate → 1-Bromo-3-methoxy-5-methylbenzene

HRID 542736

Reaction equation

HRID 542736 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH-].[Na+].S(OC)(O[CH3:16])(=O)=O>O>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH3:16])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 126484093-Bromo-5-methylphenol

Product 1

HCID 106795541-Bromo-3-methoxy-5-methylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5-bromo-3-hydroxytoluene (93 g, 0.5 m) and sodium hydroxide (21 g, 0.5 m) in water (200 ml) is stirred at 10°, treated with dimethyl sulfate (63 g, 0.5 m) over 1 hour, refluxed for 2 hours and cooled. The mixture is diluted with water and extracted with ether. The ether extract is washed, dried with sodium sulfate and concentrated in vacuo to give 5-bromo-3-methoxytoluene.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturecooled
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washis washed
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-463fc7d5baf7455d841575c1a42c4d3c
Source dataset
uspto-grants-1987_04
Patent number
US04659706

Linked notes

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