Ethanol → 2,2'-Diamino-4,4'-dibromobiphenyl

HRID 219058

Reaction equation

HRID 219058 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[N+:15]([O-])=O)=[C:4]([N+:18]([O-])=O)[CH:3]=1.CCO.[OH-].[Na+]>Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[NH2:15])=[C:4]([NH2:18])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 100466484,4'-Dibromo-2,2'-dinitro-1,1'-biphenyl

Product 1

HCID 112215382,2'-Diamino-4,4'-dibromobiphenylYield 67.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4,4′-dibromo-2,2′-dinitrobiphenyl (6.1 g, 15.17 mmol) was stirred in HCl 30 ml/EtOH 75 ml, Sn powder (7.2 g, 60.68 mmol) was added thereto, and then the reaction mixture was refluxed for 24 hours. Next, the reaction mixture was cooled to room temperature, neutralized with 10% NaOH solution, and then recrystallized in ethanol to obtain 4,4′-dibromo-2,2′-diaminobiphenyl (3.5 g, 67%). MS [M+H] 341.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was refluxed for 24 hours
  3. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-a89cd0efccb94178802fdbdc758cbc25
Source dataset
uspto-grants-2012_06
Patent number
US08198801B2

Linked notes

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