Nitric Acid → HCID 90332499, compound

HRID 595589Notes

Reaction equation

HRID 595589 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:12][CH2:11]3)=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]=2[CH:18]=1.[N+:19]([O-])([OH:21])=[O:20]>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:12][CH2:11]3)=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 90332535HCID 90332535, compound

Product 1

HCID 90332499HCID 90332499, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound ethyl 5-bromo-2-cyclopropylbenzofuran-3-carboxylate (10 g, 34 mmol) in CHCl3 (60 mL), fuming HNO3 (12 mL, 95%) was added dropwise at −20° C. over 90 min and the mixture was 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 (aq.) and brine. The solvent was removed by distillation to provide the crude product of ethyl 5-bromo-2-cyclopropyl-6-nitrobenzofuran-3-carboxylate (4.5 g, yield: 40%). 1H-NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.95 (s, 1H), 4.46 (q, J=7.2 Hz, 2H), 3.06˜3.10 (m, 1H), 1.46 (t, J=7.2 Hz, 3H), 1.34˜1.36 (m, 2H), 1.28˜1.32 (m, 2H). MS (M+H)+: 354/356.

Workup

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

Sources & evidence

ORD record
ord-10ac7af04ebb46b1b88e9dd11e43abfa
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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