Methyl 2-(bromomethyl)-3-nitrobenzoate → 4-Nitrophthalide

HRID 1789124Notes

Reaction equation

HRID 1789124 reaction equation
BrC[C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>O1CCOCC1.O>[N+:13]([C:12]1[C:3]2[CH2:8][O:7][C:5](=[O:6])[C:4]=2[CH:9]=[CH:10][CH:11]=1)([O-:15])=[O:14]

Participants

4

Reactant 1

HCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoate

Product 1

HCID 12116924-NitrophthalideYield 59.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 54.8 g of methyl 2-bromomethyl-3-nitrobenzoate in a mixture of 200 ml dioxane and 45 ml water was refluxed for 72 hours. The reaction solution was cooled and concentrated in vacuo. The resulting solid was slurried in water, collected, washed with water and dried. Recrystallization from 1-chlorobutane gave 21.4 g of 1,3-dihydro-4-nitrobenzo[c]furan-1-one, m.p. 133.5°-136°.

Workup

  1. temperaturewas refluxed for 72 hours
  2. temperatureThe reaction solution was cooled
  3. concentrationconcentrated in vacuo
  4. customcollected
  5. washwashed with water
  6. customdried
  7. customRecrystallization from 1-chlorobutane

Sources & evidence

ORD record
ord-16231784b9784304b58199bd7c4f5769
Source dataset
uspto-grants-1987_08
Patent number
US04687508

Reaction notes

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