Hydrochloric Acid → Methyl 2-bromo-5-methoxybenzoate

HRID 1363406Notes

Reaction equation

HRID 1363406 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[Br:11].[H-].[Na+].S(OC)(O[CH3:19])(=O)=O.Cl>O1CCOCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([O:10][CH3:19])[CH:7]=[CH:6][C:5]=1[Br:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 189336882-broMo-5-hydroxybenzoic acid Methyl ester

Product 1

HCID 2776849Methyl 2-bromo-5-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound of example 152 (6.5 g, 28.1 mmol) was dissolved in dry 1,4-dioxane (50 mL) under dry N2 atmosphere. To this solution, NaH (50%, 3.37 g, 70.20 mmol) was added in portions at 25° C. and the mixture was stirred for 10 min. Dimethyl sulfate (4 mL, 5.31 g, 40.48 mmol) was added and the reaction mixture was stirred at 50° C. for 1 h. It was poured into ice water, acidified using 6N HCl and extracted using EtOAc (3×100 mL). The organic extract was washed with water, dried (anhydrous Na2SO4), concentrated and purified using a silica gel column and 5% EtOAc in petroleum ether (60-80° C.) as eluant to obtain the title compound.

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for 1 h
  2. extractionextracted
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated
  7. custompurified
  8. customa silica gel column and 5% EtOAc in petroleum ether (60-80° C.)

Sources & evidence

ORD record
ord-60ca07a070dc49a9a0682f65949e2b44
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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