Methanol → Methyl 3-amino-5-bromothiophene-2-carboxylate

HRID 2364070Notes

Reaction equation

HRID 2364070 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([NH:11]C(=O)C(F)(F)F)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CO>O>[NH2:11][C:4]1[CH:3]=[C:2]([Br:1])[S:6][C:5]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 56965789Methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

Product 1

HCID 20158931Methyl 3-amino-5-bromothiophene-2-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 5-bromo-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate (8.15 g, 24.5 mmol), potassium carbonate (4.15 g, 30 mmol), MeOH (200 mL) and water (100 mL) was stirred at room temperature for 2 h. The mixture was concentrated to about a half volume and poured into saturated aqueous NaHCO3 (300 mL). Extraction with EtOAc (300 mL), washing with brine, drying over MgSO4, filtration and concentration under reduced pressure gave the title compound as a yellow solid (5.67 g, 98%):

Workup

  1. concentrationThe mixture was concentrated to about a half volume
  2. additionpoured into saturated aqueous NaHCO3 (300 mL)
  3. extractionExtraction with EtOAc (300 mL)
  4. washwashing with brine
  5. dry with materialdrying over MgSO4, filtration and concentration under reduced pressure

Sources & evidence

ORD record
ord-70dce462504c4523ad262de8846da6b4
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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