Water → Methyl 7-nitrobenzofuran-4-carboxylate

HRID 2364660Notes

Reaction equation

HRID 2364660 reaction equation
O[CH:2]1[CH2:6][C:5]2=[C:7]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:4]2[O:3]1.O>P(=O)(O)(O)O>[N+:11]([C:10]1[CH:9]=[CH:8][C:7]([C:14]([O:16][CH3:17])=[O:15])=[C:5]2[C:4]=1[O:3][CH:2]=[CH:6]2)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 962WaterHCID 20738652Methyl 2-hydroxy-7-nitro-2,3-dihydrobenzofuran-4-carboxylate

Product 1

HCID 20738655Methyl 7-nitrobenzofuran-4-carboxylateYield 34%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

Methyl 2-hydroxy-7-nitro-2,3-dihydrobenzofuran-4-carboxylate 1e (2 g, 8.40 mmol) was suspended in 250 mL of 85% phosphoric acid, stirred for 10 minutes, puted into a 100° C. oil bath and stirred for another 20 minutes. The resulting reaction mixture was added with 50 mL of water, extracted with ethyl acetate (50 mL×3). The combined organic phase was washed with saturated sodium carbonate solution (50 mL×3) and saturated sodium chloride solution (50 mL×3) successively, then dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 7-nitrobenzofuran-4-carboxylate 1f (0.63 g, yield: 34.0%) as a light yellow solid.

Workup

  1. customputed into a 100° C.
  2. stirringstirred for another 20 minutes
  3. customThe resulting reaction mixture
  4. extractionextracted with ethyl acetate (50 mL×3)
  5. washThe combined organic phase was washed with saturated sodium carbonate solution (50 mL×3) and saturated sodium chloride solution (50 mL×3) successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1cd9b783f3064a1c8bac84acf9a204d4
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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