Methanol → Methyl 4-amino-3,5-dibromobenzoate

HRID 1502787Notes

Reaction equation

HRID 1502787 reaction equation
OS(O)(=O)=O.[NH2:6][C:7]1[C:15]([Br:16])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[Br:17].[CH3:18]O>>[NH2:6][C:7]1[C:8]([Br:17])=[CH:9][C:10]([C:11]([O:13][CH3:18])=[O:12])=[CH:14][C:15]=1[Br:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 119590494-amino-3,5-dibromobenzoic acid

Product 1

HCID 11001350Methyl 4-amino-3,5-dibromobenzoate

Conditions

Temperature
80 °C

Procedure

conc. H2SO4 (1.35 mL, 25.48 mmol) was added dropwise to a stirred solution of 4-amino-3,5-dibromobenzoic acid (5.0 g, 16.99 mmol) in MeOH (50 mL) at ambient temperature and the reaction mixture was then stirred at 80° C. for 8 h. The reaction mixture was allowed to cool to ambient temperature, volatiles were evaporated and ice-water was added to the residue and extracted with EtOAc. The organic layer was washed with aqueous NaHCO3 solution followed by brine and water, dried (Na2SO4), filtered and concentrated to afford the title compound as an off white solid (5.0 g, 95%): 1H NMR (300 MHz, DMSO-d6) δ 7.91 (s, 2H), 6.20 (bs, 2H), 3.78 (s, 3H); ESIMS m/z 307.0 ([M]+); IR (thin film) 3312, 2953, 1726, 595 cm−1.

Workup

  1. temperatureto cool to ambient temperature
  2. customvolatiles were evaporated
  3. additionice-water was added to the residue
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with aqueous NaHCO3 solution
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-388e555d93cb413186be5b99df13cd89
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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