Potassium Nitrate → 4-Bromo-5-nitrothiophene-2-carbaldehyde

HRID 59751

Reaction equation

HRID 59751 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[O:13])[S:10][CH:11]=1>OS(O)(=O)=O>[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[O:13])[S:10][C:11]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 877924-Bromothiophene-2-carbaldehyde

Product 1

HCID 218862814-Bromo-5-nitrothiophene-2-carbaldehydeYield 97.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of KNO3 (3.38 g, 33.4 mmol) in 96% aqueous H2SO4 (30 ml) was added to a solution of 4-bromothiophene-2-carbaldehyde (5.8 g, 30.4 mmol) in 96% aqueous H2SO4 (60 ml) over 45 minutes, maintaining the temperature below 4° C. The resulting mixture was stirred at 0° C. for 2 hrs and then at RT overnight. The reaction was poured into ice (300 ml) and the resulting precipitate was filtered and washed with water and hexane to afford 4-bromo-5-nitrothiophene-2-carbaldehyde (Int. 65) (6.987 g, 29.6 mmol).

Workup

  1. temperaturemaintaining the temperature below 4° C
  2. customat RT
  3. customovernight
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with water and hexane

Sources & evidence

ORD record
ord-17f6620fbde043578d5caed6459214fc
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Linked notes

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