Acetic Anhydride → HCID 15740989, compound

HRID 1529820Notes

Reaction equation

HRID 1529820 reaction equation
[Br:1][C:2]1[S:3][C:4]([Br:10])=[CH:5][C:6]=1[N+:7]([O-])=O.[C:11](OC(=O)C)(=[O:13])[CH3:12]>[Fe]>[Br:1][C:2]1[S:3][C:4]([Br:10])=[CH:5][C:6]=1[NH:7][C:11](=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 49618952,5-dibromo-3-nitrothiophene

Product 1

HCID 15740989HCID 15740989, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To an ice cold solution of 2,5-dibromo-3-nitrothiophene (5.0 g, 17.4 mmol, DellErba, C.; Spinelli, D. Tetrahedron, 1965, 21, 1061-1066) in acetic acid-acetic anhydride (1:1, 50 mL) was added iron powder (5.8 g, 104.5 mmol) slowly for 15 min. and stirred at rt for 4 h. After completion of the reaction, the reaction mixture was poured into ice cold water (500 mL) and stirred for 15 min. The precipitated solid was filtered, washed with water and dried. The crude product was chromatographed over silica gel column using hexane-EtOAc (95:5) as eluent to give the product as a white color solid (3.0 g, 58%), mp 114-116° C. 1H NMR (400 MHz, CDCl3): δ 7.78 (1H, s), 7.21 (1H, s), 2.20 (3H, s).

Workup

  1. customAfter completion of the reaction
  2. stirringstirred for 15 min
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe crude product was chromatographed over silica gel column

Sources & evidence

ORD record
ord-8c40ac65906143bdbd3b9b55b6c22384
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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