1-Chloro-2-nitrobenzene → 4-(2-Nitrophenyl)indan-1-one

HRID 1615013Notes

Reaction equation

HRID 1615013 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].Cl[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:23](OCC)(=O)[CH3:24]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:19]1[CH:18]=[CH:17][CH:24]=[C:23]2[C:20]=1[CH2:21][CH2:22][C:1]2=[O:4])([O-:16])=[O:15]

Participants

7

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 585449044-(2-Nitrophenyl)indan-1-one

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Potash (8.1 g, 58.7 mmol) and Pd(PPh3)4 (1.7 g, 1.5 mmol) were added to a solution of compound 44 (7.51 g, 29.1 mmol) and 4-chloro-3-nitrobenzene (4.6 g, 29.1 mmol) in a mixture of dioxane (80 mL) and water (20 mL). The mixture obtained was heated under argon to 80° C., kept at this temperature for 16 h (TLC monitoring, eluent: hexane-ethyl acetate, 1:1), cooled, filtered through Celite, and evaporated. The resulting product was dissolved in CH2Cl2 and an insoluble residue was filtered off. The resulting product was evaporated with silica gel and purified on a short thick column (eluent: hexane-CH2Cl2100:0→0:100, CH2Cl2-ethyl acetate 100:0→50:50). Compound 45 (5.0 g) was isolated and used in the next step without purification.

Workup

  1. customThe mixture obtained
  2. filtrationfiltered through Celite
  3. customevaporated
  4. dissolutionThe resulting product was dissolved in CH2Cl2
  5. filtrationan insoluble residue was filtered off
  6. customThe resulting product was evaporated with silica gel
  7. custompurified on a short thick column (eluent: hexane-CH2Cl2100:0→0:100, CH2Cl2-ethyl acetate 100:0→50:50)

Sources & evidence

ORD record
ord-f5fb65985a3941218b2eaa93dc554174
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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