3-Nitrobenzoic acid → 3-Bromo-5-nitrobenzoic acid

HRID 541735

Reaction equation

HRID 541735 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[Br:13]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Br:13][C:11]1[CH:10]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 84973-Nitrobenzoic acidHCID 67184N-bromobutanimide

Product 1

HCID 2393363-Bromo-5-nitrobenzoic acidYield 97.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

m-Nitrobenzoic acid (11.2 g, 67.0 mmol) was taken up in sulfuric acid (30 mL) and heated to 60° C. To this solution was added N-bromosuccinimide (14.3 g, 80.4 mmol) in three portions each over a 15 minute period. After stirring for 2 h, the mixture was poured into crushed ice (100 g) to precipitate a solid. The solid was filtered, washed with water followed by hexanes to give the desired product (16 g, 97%). LCMS for C7H3BrNO4 (M−H)+: m/z=244.0, 246.0.

Workup

  1. additionthe mixture was poured
  2. customto precipitate a solid
  3. filtrationThe solid was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-4bc26b81c9524c55b82a9f4fb88c2f89
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Linked notes

Loading…