2,3-Dichloronitrobenzene → HCID 12096330, compound

HRID 722400Notes

Reaction equation

HRID 722400 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

1600 ml of isopropenylmagnesium bromide at 0.5 M in THF are introduced under nitrogen and cooled to −20° C., 51.2 g of 2,3-dichloronitrobenzene in 250 ml of anhydrous THF are added and then the mixture is left with stirring at −20° C. for 1 hour. The reaction mixture is poured at −20° C. into 1 liter of saturated NH4Cl solution and diluted with Et2O and then the aqueous phase is washed twice with Et2O. The organic phases are combined and concentrated to dryness. The product is extracted with DCM and washed twice with water and then with saturated NaCl solution. It is dried and then evaporated and the residue is chromatographed on a hexane/AcOEt (95/5; v/v) mixture. This gives 24.27 g of the expected compound, m.p.=70–71° C.

Workup

  1. waitthe mixture is left
  2. washthe aqueous phase is washed twice with Et2O
  3. concentrationconcentrated to dryness
  4. extractionThe product is extracted with DCM
  5. washwashed twice with water
  6. customIt is dried
  7. customevaporated
  8. customthe residue is chromatographed on a hexane/AcOEt (95/5; v/v) mixture

Sources & evidence

ORD record
ord-97bf50d9bedf480e9adef9e2166690d2
Source dataset
uspto-grants-2006_11
Patent number
US07138424B2

Reaction notes

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