Nitric Acid → Ethyl 5-bromo-2-hydroxy-3-nitrobenzoate

HRID 1747484Notes

Reaction equation

HRID 1747484 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[OH:12])[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]([N+:14]([O-:16])=[O:15])[C:6]=1[OH:12])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4416107Ethyl 5-bromo-2-hydroxybenzoate

Product 1

HCID 59497386Ethyl 5-bromo-2-hydroxy-3-nitrobenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

5-Bromo-2-hydroxy-benzoic acid ethyl ester (40 g, 214 mmol) is suspended in sulfuric acid (200 mL) and the reaction cooled to zero in an ice bath. The reaction is equipped with an overhead stirrer and then the nitric acid (20 mL) in sulfuric acid (40 mL) is added dropwise to the solution over the course of 30 minutes. After the addition the ice bath is removed and the reaction warmed to room temperature. The reaction is stirred at room temperature for 16 hours. When complete the reaction is poured onto crushed ice and the resulting yellow solid is collected by vacuum filtration and washed with ice cold water. The solid dried in vacuum over overnight to give the 45 g (91%) of title compound that is used without further purification. LCMS (ESMS): m/z 291.1 (M+H+).

Workup

  1. temperaturethe reaction cooled to zero in an ice bath
  2. customThe reaction is equipped with an overhead stirrer
  3. customis removed
  4. additionWhen complete the reaction is poured
  5. customonto crushed ice
  6. filtrationthe resulting yellow solid is collected by vacuum filtration
  7. washwashed with ice cold water
  8. customThe solid dried in vacuum over overnight

Sources & evidence

ORD record
ord-48275105f4234b0289d4a44f0af5bd04
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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