2,3-Dichloronitrobenzene → HCID 12096330, compound

HRID 890238Notes

Reaction equation

HRID 890238 reaction equation
[C:1]([Mg]Br)([CH3:3])=[CH2:2].[Cl:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[N+:14]([O-])=O.[NH4+].[Cl-]>C1COCC1.CCOCC>[Cl:13][C:12]1[C:7]([Cl:6])=[C:8]2[C:9]([CH:2]=[C:1]([CH3:3])[NH:14]2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 185552,3-DichloronitrobenzeneHCID 25517Ammonium ChlorideHCID 178456138HCID 178456138, compound

Product 1

HCID 12096330HCID 12096330, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

1 600 ml of 0.5M isopropenylmagnesium bromide in THF are introduced under nitrogen and are cooled to −20° C., 51.2 g of 2,3-dichloronitrobenzene in 250 ml of anhydrous THF are added and the mixture is left stirring for I hour at −20° C. The reaction medium is poured at −20° C. onto 1 liter of saturated NH4Cl solution, the mixture is diluted with Et2O and then the aqueous phase is washed twice with Et2O. The organic phases are combined and are concentrated to dryness. The residue is extracted with DCM and the organic phase is washed twice with water and then with a saturated NaCl solution. It is dried and then evaporated and the residue is chromatographed on [lacuna] a hexane/AcOEt (95/5, v/v) mixture. 24.27 g of the expected compound are obtained, M.p.=70–71° C.

Workup

  1. waitthe mixture is left
  2. washthe aqueous phase is washed twice with Et2O
  3. concentrationare concentrated to dryness
  4. extractionThe residue is extracted with DCM
  5. washthe organic phase is washed twice with water
  6. customIt is dried
  7. customevaporated
  8. customthe residue is chromatographed on [lacuna] a hexane/AcOEt (95/5

Sources & evidence

ORD record
ord-7a30ae80f6cc4854a9c90617f44f539f
Source dataset
uspto-grants-2006_02
Patent number
US06995184B2

Reaction notes

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