Potassium Carbonate → 4-(4-Methoxy-2-nitrophenyl)indan-1-one

HRID 1615007Notes

Reaction equation

HRID 1615007 reaction equation
C([O-])([O-])=O.[K+].[K+].CC1(C)C(C)(C)OB([C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C:19]3=[O:24])O1.Cl[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[N+:35]([O-:37])=[O:36].CCCCCC.C(OCC)(=O)C>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>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C:19]3=[O:24])=[C:28]([N+:35]([O-:37])=[O:36])[CH:29]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 251404-Chloro-3-nitroanisoleHCID 21226206Ethyl acetate hexaneHCID 220320882,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-1-one

Product 1

HCID 673683614-(4-Methoxy-2-nitrophenyl)indan-1-one

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

Potash (7.5 g, 54.3 mmol) and Pd(PPh3)4 (1.6 g, 1.4 mmol) were added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indan-1-one 34 (7.0 g, 27.1 mmol) and 4-chloro-3-nitroanisole (5.1 g, 27.1 mmol) in a mixture of dioxane (80 mL) and water (20 mL). The mixture obtained was heated to 80° C. under argon, kept at this temperature for 16 h (TLC monitoring, eluent: hexane-ethyl acetate, 1:1), cooled, filtered through Celite, evaporated, and dissolved in CH2Cl2. Then the mixture was filtered off from the insoluble portion, evaporated with silica gel, and purified on a short thick column with silica gel (eluent: hexane-CH2Cl2 100:0→0:100, CH2Cl2-ethyl acetate 100:0→50:50). Yield of 35: 5.59 g. The product was used in the next step without additional purification.

Workup

  1. customThe mixture obtained
  2. filtrationfiltered through Celite
  3. customevaporated
  4. dissolutiondissolved in CH2Cl2
  5. filtrationThen the mixture was filtered off from the insoluble portion
  6. customevaporated with silica gel
  7. custompurified on a short thick column with silica gel (eluent: hexane-CH2Cl2 100:0→0:100, CH2Cl2-ethyl acetate 100:0→50:50)
  8. customThe product was used in the next step without additional purification

Sources & evidence

ORD record
ord-90eede362567442197342c5c4c0aeba5
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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