Methanol → Methyl 5-nitrobenzofuran-2-carboxylate

HRID 71345

Reaction equation

HRID 71345 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:7]=2[CH:8]=1)([OH:3])=[O:2].OS(O)(=O)=O.[CH3:21]O>>[CH3:21][O:2][C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:7]=2[CH:8]=1)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14771285-Nitrobenzofuran-2-carboxylic acid

Product 1

HCID 12148807Methyl 5-nitrobenzofuran-2-carboxylate

Conditions

Temperature
60 °C

Procedure

A mixture of 2-carboxy-5-nitrobenzofuran (2.0 g), MeOH (10 mL) and Concentrated H2SO4 (2.1 mL) was heated in a sealed tube at 60° C. for 3 h. Upon cooling to the room temperature it was quenched with ice-water and carefully basified with addition of NaHCO3. The solid obtained was filtered, washed with water, dried and analyzed to give 2-methoxycarbonyl-5-nitrobenzofuran. 1H NMR (CDCl3): δ 8.66 (d, 1H, J=2.4 Hz), 8.36 (dd, 1H, J=2.4 and 9.6 Hz), 7.71 (d, 1H, J=9.3 Hz), 7.65 (s, 1H), 4.01 (s, 3H); LCMS: purity: 97%; MS (m/e): 222 (MH+).

Workup

  1. temperatureUpon cooling to the room temperature it
  2. customwas quenched with ice-water
  3. additioncarefully basified with addition of NaHCO3
  4. customThe solid obtained
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-909458d1822549e08c27ccc6ebd3b281
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Linked notes

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