Dimethyl Sulfate → Benzene, 1,3-dibromo-2-methoxy-

HRID 1042508

Reaction equation

HRID 1042508 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].[C:10](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 118472,6-Dibromophenol

Product 1

HCID 181584Benzene, 1,3-dibromo-2-methoxy-Yield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,6-dibromophenol (25 g, 0.099 mol), powder potassium carbonate (28 g, 0.2 mol, 2 equiv) and dimethyl sulfate (12.6 g, 0.099 mol) in acetonitrile (400 mL) was kept at reflux with good stirring for 4 hr. After cooling, the solids were removed by filtration and the solvent was removed in a rotary evaporator. The residue was taken in 2:1 heptane/ethyl acetate mixture (800 mL) and washed with water (2×400 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was removed in a rotary evaporator, leaving almost pure 1 (15.5 g, 96%).

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. customthe solids were removed by filtration
  4. customthe solvent was removed in a rotary evaporator
  5. washwashed with water (2×400 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed in a rotary evaporator

Sources & evidence

ORD record
ord-99facb1a8b3543a985521627d332adbc
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Linked notes

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