Methanol--water (1/1) → Methyl 3-amino-5-bromothiophene-2-carboxylate

HRID 1916356Notes

Reaction equation

HRID 1916356 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.CO.O>C([O-])([O-])=O.[K+].[K+]>[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([NH2:11])[CH:3]=1

Participants

4

Reactant 2

HCID 22242641Methanol--water (1/1)HCID 56965789Methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

Product 1

HCID 20158931Methyl 3-amino-5-bromothiophene-2-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

Methyl 5-bromo-3-(trifluoroacetylamino)-2-thiophenecarboxylate (2.0 g, 6.2 mmol) was stirred in 120 mL of 0.25 N K2CO3 in 7:3 MeOH/water. After 2.5 h, the bulk of the MeOH was removed in vacuo. The residue was partitioned between brine (75 mL) and CH2Cl2 (100 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to provide methyl 5-bromo-3-amino-2-thiophenecarboxylate as a yellow solid (1.4 g, 100%).

Workup

  1. customthe bulk of the MeOH was removed in vacuo
  2. customThe residue was partitioned between brine (75 mL) and CH2Cl2 (100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35954111250448da81286aa2ce179c1a
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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