Nitric Acid → 4-Bromomethyl-3-nitrobenzoic acid

HRID 1007743Notes

Reaction equation

HRID 1007743 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[N+:12]([O-])([OH:14])=[O:13]>>[N+:12]([C:4]1[CH:5]=[C:6]([C:9]([OH:11])=[O:10])[CH:7]=[CH:8][C:3]=1[CH2:2][Br:1])([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 225994-(Bromomethyl)benzoic acid

Product 1

HCID 1323864-Bromomethyl-3-nitrobenzoic acidYield 85%

Conditions

Temperature
-10 °C

Procedure

α-Bromo-p-toluic acid (21.5 g, 100 mmol) was added in five equal portions to 90% HNO3 (250 mL) at −10° C. The reaction mixtures were stirred at −10° C. for 3 h and poured into ice-water. After stirring at room temperature for 3 h, the white precipitate was filtered, collected and dried by air overnight to give ortho-nitro α-bromo-p-toluic acid (22.2 g, 85%) as slightly yellow solid.

Workup

  1. customThe reaction mixtures
  2. stirringAfter stirring at room temperature for 3 h
  3. filtrationthe white precipitate was filtered
  4. customcollected
  5. customdried by air overnight

Sources & evidence

ORD record
ord-1198aa666f804fe486712d26a373d62c
Source dataset
uspto-grants-2004_09
Patent number
US06797522B1

Reaction notes

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