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

HRID 1503797Notes

Reaction equation

HRID 1503797 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 brought to ambient temperature, volatiles were evaporated and ice cold water was added to the residue and which was then extracted with EtOAc. The organic layer was washed with an aqueous NaHCO3 solution followed by brine and water. The solution was then 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. customwas brought to ambient temperature
  2. customvolatiles were evaporated
  3. additionice cold water was added to the residue and which
  4. extractionwas then extracted with EtOAc
  5. washThe organic layer was washed with an aqueous NaHCO3 solution
  6. dry with materialThe solution was then dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-df45966d37da4fa197a9dd3f5d08e840
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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