Nitric Acid → Ethyl 5-bromo-6-nitrobenzofuran-3-carboxylate

HRID 595533Notes

Reaction equation

HRID 595533 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:6]=2[CH:15]=1.[N+:16]([O-])([OH:18])=[O:17]>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 21694192Ethyl 5-bromo-1-benzofuran-3-carboxylate

Product 1

HCID 90332392Ethyl 5-bromo-6-nitrobenzofuran-3-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 5-bromobenzofuran-3-carboxylate (95 g, 353 mmol) in CHCl3 (1000 mL), fuming HNO3 (192 mL, 95%) was added dropwise at −20° C. over 90 min and stirred at 0° C. for 1 hour. The reaction mixture was added to ice water and extracted with CH2Cl2. The organic layer was washed with NaHCO3 and brine. The solvent was removed by distillation to provide the crude product of ethyl 5-bromo-6-nitrobenzofuran-3-carboxylate (95 g, yield: 85%). It was used for the next step without further purification.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with NaHCO3 and brine
  3. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-1d27b97a83f24b739b659763561d1eaf
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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