Chloroform → HCID 21199122, compound

HRID 1066282

Reaction equation

HRID 1066282 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[Br:11]Br.C(Cl)(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>O>[Br:11][C:9]1[C:2]([CH3:1])=[C:3]([C:6]([CH3:10])=[CH:7][CH:8]=1)[C:4]#[N:5]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 24408BromineHCID 810572,6-DimethylbenzonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21199122HCID 21199122, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,6-dimethylbenzonitrile (5.0 g, 38.0 mmol), bromine (1.9 ml, 38.0 mmol) and chloroform (10 ml) is stirred at room temperature for 24 hours and subsequently heated to 60° C. for 6 hours. Upon cooling down to 0° C., 10 g of AlCl3 are added and the mixture is stirred for 4 hours at 0° C. The reaction mixture is poured into water and extracted with toluene. The organic phase is separated and concentrated and the residue is purified by column chromatography yielding the pure product as brown crystals, 6.2 g, mp. 60° C.

Workup

  1. temperaturesubsequently heated to 60° C. for 6 hours
  2. temperatureUpon cooling down to 0° C.
  3. stirringthe mixture is stirred for 4 hours at 0° C
  4. extractionextracted with toluene
  5. customThe organic phase is separated
  6. concentrationconcentrated
  7. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-c743b4deb59541ecad943013fd7950f7
Source dataset
uspto-grants-2001_06
Patent number
US06242498B1

Linked notes

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