5-Bromo-3-nitro-thiophene-2-carbaldehyde → 5-Bromo-3-nitrothiophene-2-carboxylic acid

HRID 1181347Notes

Reaction equation

HRID 1181347 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]=[O:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.CC(C)=[O:14].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.O>[Br:1][C:2]1[S:6][C:5]([C:7]([OH:14])=[O:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 2

HCID 862474935-Bromo-3-nitro-thiophene-2-carbaldehydeHCID 131709961Jones' reagent

Product 1

HCID 299455455-Bromo-3-nitrothiophene-2-carboxylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

5Bromo-3-nitrothiophene-2-carbaldehyde (0.5953 g, 2.5012 mmol, prepared according to Sone, C; Matsuki, Y Bull Chem Soc Japan, 1963, 36(5), 618-20.) was dissolved in acetone (5 mL) and Jones Reagent (1.5 mL) was added. The reaction was stirred at RT for 1 h. The reaction was diluted with water (30 mL) and extracted with EtOAc (3×30 mL). The combined organics were washed With water (4×100 mL), dried over MgSO4 filtered and concentrated to give 0.4993 g (1.9892 mmol, 80%) of the product as a light yellow solid.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organics were washed With water (4×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3e7345aab5a9475e996762caf0632f32
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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