1-Chloro-4-iodobenzene → HCID 66957737, compound

HRID 1470807Notes

Reaction equation

HRID 1470807 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)#[CH:2].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1.N1CCC[C@H]1C(O)=O.O=C1O[C@H]([C@H](CO)O)C(O)=C1O.[N-:39]=[N+:40]=[N-:41].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CS(C)=O.O.[O-]S([O-])(=O)=O.[Cu+2]>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:39]2[CH:2]=[C:1]([C:3]3[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=3)[N:41]=[N:40]2)=[CH:14][CH:13]=1

Participants

10

Reactant 6

HCID 125101-Chloro-4-iodobenzeneHCID 24436Sodium SulfateHCID 33557Sodium AzideHCID 145742L-ProlineHCID 45472454-EthynylbenzonitrileHCID 54670067L-Ascorbic Acid

Product 1

HCID 66957737HCID 66957737, compoundYield 48.9%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Following the procedure published by Feldman et al. (Org. Lett. 2004, 6, 3897), a suspension of 4-ethynylbenzonitrile (50 mg, 0.393 mmol), 1-chloro-4-iodobenzene (94 mg, 0.393 mmol), L-proline (9 mg, 0.079 mmol), ascorbic acid (7 mg, 0.039 mmol), NaN3 (31 mg, 0.472 mmol), CuSO4 (3 mg, 0.020 mmol), and Na2SO4 (11 mg, 0.079 mmol) in DMSO (1.5 mL) was heated at 65° C. for 24 h. Upon cooling the mixture was diluted with H2O and stirred for 30 min at ambient temperature. The intermediate 4-[1-(4-chloro-phenyl)-1H-[1,2,3]triazol-4-yl]-benzonitrile (54 mg, 48%) was then obtained by vacuum filtration after washing with copious volumes of H2O and 20% NH4OH (˜20 mL). Reduction to the aldehyde was then conducted under conditions previously described.

Workup

  1. temperatureUpon cooling the mixture

Sources & evidence

ORD record
ord-67aeceef8f544aaea937c383b0752654
Source dataset
uspto-grants-2015_04
Patent number
US09006468B2

Reaction notes

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