O-Phenylenediamine → 2,3-Bis(bromomethyl)quinoxaline

HRID 892410

Reaction equation

HRID 892410 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Br:9][CH2:10][C:11](=O)[C:12](=O)[CH2:13][Br:14]>C1C=CC=CC=1>[Br:9][CH2:10][C:11]1[C:12]([CH2:13][Br:14])=[N:8][C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:7]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 227471,4-Dibromo-2,3-butanedione

Product 1

HCID 184492,3-Bis(bromomethyl)quinoxalineYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1,2-phenylenediamine (0.1 mole, 10.8 g) and 1,4-dibromo-2,3-butanedione (0.1 mole, 24.4 g) was refluxed in benzene (200 mL) using a Dean-Stark trap for one hour. The reaction mixture was then evaporated to dryness in vacuo and the residue flash chromatographed on silica gel (15:1). Elution with 15% hexane/chloroform afforded 29.38 g of 2,3-bis(bromomethyl)quinoxaline, m.p. 150°-151° C.; 1H NMR (CDCl3, 200 MHz): δ4.92 (s, 4H, CH2), 7.8 (m, 2H, ArH), 8.05 (m, 2H, ArH).

Workup

  1. customfor one hour
  2. customThe reaction mixture was then evaporated to dryness in vacuo
  3. customthe residue flash chromatographed on silica gel (15:1)
  4. washElution with 15% hexane/chloroform

Sources & evidence

ORD record
ord-274c2e08a5994e4fa1cbba20d36b6112
Source dataset
uspto-grants-1992_06
Patent number
US05118675

Linked notes

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