Ethanol → Ethyl 2-amino-3-bromo-5-methylbenzoate

HRID 1425440

Reaction equation

HRID 1425440 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 27744002-Amino-3-bromo-5-methylbenzoic acid

Product 1

HCID 54594338Ethyl 2-amino-3-bromo-5-methylbenzoateYield 64%

Procedure

Ethanol (10 mL) was added to 2-amino-3-bromo-5-methylbenzoic acid (1.00 g, 4.4 mmol). While the mixture was stirred, thionyl chloride (1.03 g, 8.7 mmol) was added at room temperature, followed by stirring at 80° C. overnight. The reaction solution was concentrated, and then diluted with water under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=0/10, 4/6) to obtain 715 mg of the title compound as a pale yellow solid (64%).

Workup

  1. stirringby stirring at 80° C. overnight
  2. concentrationThe reaction solution was concentrated
  3. additiondiluted with water under ice-
  4. temperaturecooling
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=0/10, 4/6)

Sources & evidence

ORD record
ord-536cf4a9793244299424c2221607ffff
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Linked notes

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