Chlorosuccinimide → HCID 19759392, compound

HRID 1586783Notes

Reaction equation

HRID 1586783 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[Cl:13]N1C(=O)CCC1=O>O1CCCC1>[Cl:13][C:9]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 2724261-(4-Methylphenyl)-1H-pyrrole

Product 1

HCID 19759392HCID 19759392, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 1-(4-methylphenyl)pyrrole (1 g) in tetrahydrofuran (50 ml) was added N-chlorosuccinimide (850 mg) in one portion at -78° C. under nitrogen atmosphere. The mixture was warmed to 10° C., stirred for one hour, and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to yield 2-chloro-1-(4-methylphenyl)pyrrole (1.2 g) as an oil. (This product was a mixture of the starting material and the desired product and used to the next reaction furthermore without purification.)

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-e865b163c88642b5a2904c6bd2f8fb43
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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