Ammonia → 2-Bromo-4,6-dinitroaniline

HRID 712155

Reaction equation

HRID 712155 reaction equation
O.[N+:2]([C:5]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:6]=1[NH2:7])([O-:4])=[O:3].[Br:15]Br.N>C(O)(=O)C>[Br:15][C:8]1[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:5]([N+:2]([O-:4])=[O:3])[C:6]=1[NH2:7]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 73212,4-DinitroanilineHCID 24408Bromine

Product 1

HCID 157522-Bromo-4,6-dinitroanilineYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred mixture of water (3.75 L) and acetic acid (375 mL) at rt was added 2,4-dinitroaniline (500 g, 2.73 mol) followed by dropwise addition of bromine (210 mL, 4.09 mol) over 30 min. The reaction mixture was stirred at rt for 15 min then heated to 100° C. for 2 h. The reaction mixture was then cooled to rt poured onto ice-cold water (5-6 L) and basified (pH 8-10) with aqueous ammonia. The solid thus obtained was filtered, washed with cold water and dried under vacuum. The resulting solid was washed with n-pentane to give the desired product (600 g, 84%).

Workup

  1. temperaturethen heated to 100° C. for 2 h
  2. temperatureThe reaction mixture was then cooled to rt
  3. additionpoured onto ice-cold water (5-6 L)
  4. customThe solid thus obtained
  5. filtrationwas filtered
  6. washwashed with cold water
  7. customdried under vacuum
  8. washThe resulting solid was washed with n-pentane

Sources & evidence

ORD record
ord-0bbc4b2c48de4f10b61d6400c7c470a2
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Linked notes

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