Sodium Hydroxide → HCID 59520005, compound

HRID 1162080Notes

Reaction equation

HRID 1162080 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:16]([O-:18])=[O:17])[C:5]2[O:9][CH:8]=[C:7]([C:10]([O:12]CC)=[O:11])[C:6]=2[CH:15]=1.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:16]([O-:18])=[O:17])[C:5]2[O:9][CH:8]=[C:7]([C:10]([OH:12])=[O:11])[C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59520007HCID 59520007, compound

Product 1

HCID 59520005HCID 59520005, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-bromo-7-nitro-1-benzofuran-3-carboxylate (5.5 g, 17.5 mmol; obtained in Step 1) was suspended in ethanol (20 mL). 2 M NaOH (20 mL) was added and the mixture was heated at reflux for 2 h. The ethanol was removed by evaporation and the remaining solution acidified with concentrated HCl (4 mL), diluted with water and the product collected by filtration, washed with water and dried in a vacuum oven. Yield: 4.65 g (93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.43 (s, 1H) 8.26 (d, J=1.8 Hz, 1H) 8.34 (d, J=2.0 Hz, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe ethanol was removed by evaporation
  4. additiondiluted with water
  5. filtrationthe product collected by filtration
  6. washwashed with water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-b3a8b75ec955490aa8cdf387b9f45388
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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