Sodium Hydroxide → 5-Bromo-3-nitrothiophene-2-carboxylic acid

HRID 532461Notes

Reaction equation

HRID 532461 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[S:8][C:9]([Br:15])=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])=[O:6]>C1COCC1.CO>[Br:15][C:9]1[S:8][C:7]([C:5]([OH:6])=[O:4])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57618723Methyl 5-bromo-3-nitrothiophene-2-carboxylate

Product 1

HCID 299455455-Bromo-3-nitrothiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1N sodium hydroxide solution (4 mL) was added to a solution of 5-bromo-3-nitrothiophene-2-carboxylic acid methyl ester (975 mg) in 1:1 THF/methanol (4 mL) and the solution was stirred at room temperature for 1 h. The solution was partitioned between water and ethyl acetate. The aqueous phase was brought to pH 1 with 2N HCl, extracted with ethyl acetate, dried over magnesium sulfate and concentrated. The product with the molecular weight of 252.04 (C5H2BrNO4S) was obtained in this way; MS (ESI): 252 and 254 (M+H+).

Workup

  1. customThe solution was partitioned between water and ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product with the molecular weight of 252.04 (C5H2BrNO4S) was obtained in this way

Sources & evidence

ORD record
ord-a5173de61bd34eaa81107fe602adecec
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

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