4-Bromophenylhydrazine hydrochloride → HCID 19041651, compound

HRID 1721370Notes

Reaction equation

HRID 1721370 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:9]([C:6]2[CH:7]=[CH:8][C:3]([Br:2])=[CH:4][CH:5]=2)[NH2:10])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 685274-Bromobenzyl bromide

Product 1

HCID 19041651HCID 19041651, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Bromophenylhydrazine hydrochloride (30 g, 134 mmol), p-bromobenzyl bromide (40 g, 161 mmol), disopropylethylamine (43 g, 335 mmol) and tetrabutylammonium bromide (13 g, 40 mmol) were stirred together in 400 mL of CH2Cl2 at r.t. overnight. The mixture was then washed with H2O, dried over MgSO4 and the title product was purified by flash chromatography on silica using EtOAc:hexane (30:70) and by a swish in hexanes. Yield 34 g (71%).

Workup

  1. washThe mixture was then washed with H2O
  2. dry with materialdried over MgSO4
  3. customthe title product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-03444f0a131f4e21972214be57b3e021
Source dataset
uspto-grants-1996_04
Patent number
US05510368

Reaction notes

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