Methanol → Benzoic acid, 5-bromo-3-fluoro-2-hydroxy-4-methoxy-, methyl ester

HRID 629480Notes

Reaction equation

HRID 629480 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([F:12])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.O.[CH3:20]O>>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([F:12])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:20])=[O:8]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 848075045-Bromo-3-fluoro-2-hydroxy-4-methoxybenzoic acid

Product 1

HCID 118468351Benzoic acid, 5-bromo-3-fluoro-2-hydroxy-4-methoxy-, methyl ester

Conditions

Temperature
70 °C

Procedure

To a solution of 5-bromo-3-fluoro-2-hydroxy-4-methoxybenzoic acid (0.70 g) in methanol (15.0 mL) was added dropwise thionyl chloride (0.39 mL) under ice-cooling. The reaction solution was stirred at 70° C. for 15 hr under argon atmosphere, and then overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.52 g).

Workup

  1. temperaturecooling
  2. customovernight
  3. customat room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-87390531e9e8444086375d648407b097
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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