Cyclohexene → HCID 20333854, compound

HRID 1703478Notes

Reaction equation

HRID 1703478 reaction equation
Br[C:2]1[O:3][C:4]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:5]=2[C:6]=1[C:7]1[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=1.C1CCCCC=1.[N+:28]([O-:33])([N+]([O-])=O)=[O:29]>C(Cl)(Cl)Cl>[Cl:21][C:18]1[CH:19]=[CH:20][C:4]2[O:3][C:2]([N+:28]([O-:33])=[O:29])=[C:6]([C:7]3[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=3)[C:5]=2[CH:17]=1

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25352Nitrogen oxide (N2O4)HCID 20333853HCID 20333853, compound

Product 1

HCID 20333854HCID 20333854, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3-(2-bromo-5-chloro-3-benzofuranyl)-phenylacetic acid in chloroform with 1.5 equivalents of cyclohexene is treated with 1.5 equivalents of dinitrogen tetroxide and stirred for about 20 hours at room temperature. The mixture is washed with water, extracted with saturated sodium bicarbonate solution, then the aqueous extracts are acidified. The mixture is extracted with dichloromethane, which is dried and concentrated. The residue is recrystallized from a mixture of benzene and hexane to provide 3-(5-chloro-2-nitro-3-benzofuranyl)phenylacetic acid.

Workup

  1. washThe mixture is washed with water
  2. extractionextracted with saturated sodium bicarbonate solution
  3. extractionThe mixture is extracted with dichloromethane, which
  4. customis dried
  5. concentrationconcentrated
  6. customThe residue is recrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-6cdbee8f698f47e9aae7b7889996c683
Source dataset
uspto-grants-1978_11
Patent number
US04124605

Reaction notes

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