Dichloromethane → 4-Bromo-5-nitrothiophene-2-carbaldehyde

HRID 723228Notes

Reaction equation

HRID 723228 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.C(Cl)Cl>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

5

Reactant 3

HCID 6344DichloromethaneHCID 24434Potassium NitrateHCID 877924-Bromothiophene-2-carbaldehyde

Product 1

HCID 218862814-Bromo-5-nitrothiophene-2-carbaldehydeYield 98.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of potassium nitrate (110 g, 1.09 mol) in H2SO4 (550 mL, conc.) was added to a solution of 4-bromo-thiophene-2-carbaldehyde (207.6 g, 1.08 mol) in H2SO4 (1.1 L, conc.) at CH2Cl2 (5 mL, anhydrous) at 0° C. over a 45 minute period. The reaction mixture was stirred 0° C. for 2 hrs, then stirred overnight at rt. The reaction mixture was poured over ice, filtered, and washed with water and hexanes. The yellow solid was dried overnight to afford the title compound (251.4 g, 98.6%). 1H-NMR (DMSO-d6): δ 9.90 (s, 1H), 8.56 (s, 1H).

Workup

  1. stirringstirred overnight at rt
  2. additionThe reaction mixture was poured over ice
  3. filtrationfiltered
  4. washwashed with water and hexanes
  5. customThe yellow solid was dried overnight

Sources & evidence

ORD record
ord-d103f6c77f19491694048527fd202014
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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