Cyclohexene → HCID 178418484, compound

HRID 618750Notes

Reaction equation

HRID 618750 reaction equation
[Br:1]Br.[NH:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[O:15][C:16]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:17]=3[CH:18]=2)=[N:6][N:5]=[N:4]1.C1CCCCC=1>C(Cl)(Cl)(Cl)Cl.O1CCOCC1>[Br:1][C:18]1[C:17]2[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:16]=2[O:15][C:14]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[NH:3][N:4]=[N:5][N:6]=1

Participants

6

Reactant 3

HCID 8079CyclohexeneHCID 24408BromineHCID 178418392HCID 178418392, compound

Product 1

HCID 178418484HCID 178418484, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 11.6 g of bromine in 28 ml of carbon tetrachloride is added dropwise over the course of 35 minutes to a suspension of 10.0 g of 2-[2'-(1H-tetrazol-5-yl)-phenyl]-5-methylbenzofuran in 418 ml of dioxane. After stirring for 3 hours at room temperature, 12.6 ml of cyclohexene are added dropwise and then the reaction mixture is concentrated by evaporation in vacuo. The residue is taken up in 50 ml of 2N sodium hydroxide solution and extracted with 100 ml of ether. Three clear phases form. The two lower phases are separated off, acidified with 40 ml of 4N hydrochloric acid and extracted three times with 100 ml of ethyl acetate each time. The combined ethyl acetate phases are washed with 100 ml of brine and, after removal of the solvent in vacuo, they result in a yellow oil which yields crystalline 3-bromo-2-[2'-(1H-tetrazol-5-yl)-phenyl]-5-methylbenzofuran, m.p. 167-168°, from toluene.

Workup

  1. concentrationthe reaction mixture is concentrated by evaporation in vacuo
  2. extractionextracted with 100 ml of ether
  3. customThe two lower phases are separated off
  4. extractionextracted three times with 100 ml of ethyl acetate each time
  5. washThe combined ethyl acetate phases are washed with 100 ml of brine
  6. customafter removal of the solvent in vacuo, they
  7. customresult in a yellow oil which

Sources & evidence

ORD record
ord-f4b3d1aaa74846b38a1038a2fba32616
Source dataset
uspto-grants-1999_09
Patent number
US05955487

Reaction notes

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