Dimethyl Sulfate → Ethyl 3-bromo-2-methoxy-6-methylbenzoate

HRID 2177755Notes

Reaction equation

HRID 2177755 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[Br:8][C:9]1[C:10](O)=[C:11]([C:17]([CH3:20])=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:8][C:9]1[C:10]([O:6][CH3:7])=[C:11]([C:17]([CH3:20])=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 11470920Ethyl 3-bromo-2-hydroxy-6-methylbenzoate2×

Product 1

HCID 11459983Ethyl 3-bromo-2-methoxy-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dimethyl sulphate (2.3 ml) was added to a suspension of ethyl 3-bromo-2-hydroxy-6-methylbenzoate (Intermediate 92, 5.19 g) and potassium carbonate (5.64 g) in dry acetone (70 ml) and the resultant mixture was stirred and heated at reflux for 2 hours. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in ether and washed with NaHCO3 (saturated aqueous solution), dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give crude ethyl 3-bromo-2-methoxy-6-methylbenzoate (5.4 g) as a colourless oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. dissolutionThe residue was dissolved in ether
  6. washwashed with NaHCO3 (saturated aqueous solution)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-580fd5f4668b4886877e707c2afd43aa
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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