Formic Acid → 5-Bromo-2-nitrothiophene-3-carbaldehyde

HRID 1967146

Reaction equation

HRID 1967146 reaction equation
[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([CH:10](Cl)Cl)[CH:3]=1.C(O)=[O:14]>[Cl-].[Zn+2].[Cl-].O>[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([CH:10]=[O:14])[CH:3]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 595256075-Bromo-3-(dichloromethyl)-2-nitrothiophene

Product 1

HCID 534029475-Bromo-2-nitrothiophene-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

5-Bromo-3-(dichloromethyl)-2-nitrothiophene (60.5 g, 208 mmol) and zinc chloride (113 g, 832 mmol) were stirred in refluxing formic acid (800 mL) overnight. After cooling to ambient temperature, water was added and the mixture was extracted with EtOAc (4×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as an orange solid.

Workup

  1. extractionthe mixture was extracted with EtOAc (4×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f68080b21a334d46956aa02fd6a2cd4c
Source dataset
uspto-grants-2013_04
Patent number
US08420695B2

Linked notes

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