Tert-Butyl hypochlorite → HCID 19759344, compound

HRID 248371Notes

Reaction equation

HRID 248371 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1.[Cl:15]OC(C)(C)C>C(Cl)(Cl)(Cl)Cl>[Cl:15][C:11]1[CH:10]=[C:9]([C:13]#[N:14])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 27977151-(4-Methylphenyl)pyrrole-2-carbonitrile

Product 1

HCID 19759344HCID 19759344, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a stirred mixture of 1-(4-methylphenyl)pyrrole-2-carbonitrile (10 g), silica gel (46 g) and carbon tetrachloride (150 ml) was added dropwise a solution of tertbutyl hypochlorite (8.1 g) in carbon tetrachloride (15 ml). After stirring for 1 hour at ambient temperature, the precipitate was filtered off and the filtrate was evaporated in vacuo to give an oily residue which was crystallized from n-hexane. The crystals were further purified by silica gel column chromatography (SiO2 100 g, n-hexane-toluene=1:1) and subsequent crystallization from n-hexane to give colorless crystals (3.92 g) of 4-chloro-1-(4-methylphenyl)pyrrole-2-carbonitrile.

Workup

  1. filtrationthe precipitate was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customto give an oily residue which
  4. customwas crystallized from n-hexane
  5. customThe crystals were further purified by silica gel column chromatography (SiO2 100 g, n-hexane-toluene=1:1) and subsequent crystallization from n-hexane

Sources & evidence

ORD record
ord-1e6be576ed0e49e8bd04c4876feafe63
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

Loading…