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

HRID 2216183Notes

Reaction equation

HRID 2216183 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-3fa3140a8e1d4a76ae12f6c454f50d9b
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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