Chloroform → HCID 83747840, compound

HRID 628515Notes

Reaction equation

HRID 628515 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([CH3:14])[N:11]([CH3:15])[N:10]=2)=[CH:5][C:4]=1[CH3:16].[Br:17]N1C(=O)CCC1=O.C(Cl)(Cl)Cl>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([Br:17])=[C:12]([CH3:14])[N:11]([CH3:15])[N:10]=2)=[CH:5][C:4]=1[CH3:16]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 67184N-bromobutanimideHCID 118001329HCID 118001329, compound

Product 1

HCID 83747840HCID 83747840, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, a mixture of 3-(4-methoxy-3-methyl-phenyl)-1,5-dimethyl-1H-pyrazole (described in Reference Preparation example 43) 5.9 g, N-bromosuccinimide 5.8 g and chloroform 100 ml was stirred for seventeen hours. To the reaction mixture was added water and the resulting mixture was extracted with chloroform. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 3-(4-methoxy-3-methyl-phenyl)-4-bromo-1,5-dimethyl-1H-pyrazole 4.0 g.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-62f5365ee7294be68471df736be89ed1
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

Loading…