Acetic Anhydride → 4-Bromo-5-nitrothiophene-2-carbonitrile

HRID 723230Notes

Reaction equation

HRID 723230 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[N:11]O)[S:5][C:6]=1[N+:7]([O-:9])=[O:8].C(OC(=O)C)(=O)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:10]#[N:11])[S:5][C:6]=1[N+:7]([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 738521524-Bromo-5-nitro-thiophene-2-carbaldehyde oxime

Product 1

HCID 218213104-Bromo-5-nitrothiophene-2-carbonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromo-5-nitro-thiophene-2-carbaldehyde oxime (216 g, 0.86 mol, Example 286: step b) and acetic anhydride (1 L, 10.6 mol) was heated to reflux for 4 hrs. The reaction mixture was cooled to rt and the solvents were removed in vacuo. The crude reaction mixture was diluted in methylene chloride and washed with water. The organic layer was dried over magnesium sulfate and concentrated in vacuo resulting in a residue, which was stirred in diethyl ether/hexanes and filtered to afford the title compound as a yellow solid (170.2 g, 85%). 1H-NMR (DMSO-d6): δ 8.25 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hrs
  3. customthe solvents were removed in vacuo
  4. customThe crude reaction mixture
  5. washwashed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customresulting in a residue, which
  9. filtrationfiltered

Sources & evidence

ORD record
ord-2178a8077733415c8557e51e097096aa
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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