Toluene → 4-(2-Nitrophenyl)indan-1-one

HRID 1615035Notes

Reaction equation

HRID 1615035 reaction equation
C1(C)C=CC=CC=1.CC1(C)C(C)(C)OB([C:16]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:17]=2[CH2:18][CH2:19][C:20]3=[O:25])O1.Cl[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N+:34]([O-:36])=[O:35].C([O-])([O-])=O.[Na+].[Na+]>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.CCOC(C)=O.O>[N+:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][CH2:19][C:20]2=[O:25])([O-:36])=[O:35]

Participants

8

Reactant 4

HCID 1140TolueneHCID 69451-Chloro-2-nitrobenzeneHCID 10340Sodium CarbonateHCID 220320882,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-1-one

Product 1

HCID 585449044-(2-Nitrophenyl)indan-1-oneYield 91.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Degassed toluene (0.5 L), borolan 88 (10 g, 39 mmol), 2-chloro-1-nitrobenzene (6.3 g, 40 mmol), Pd(PPh3)4 (3 g, 2.6 mmol) and 2M Na2CO3 (200 mL) were mixed under a rapid flow of argon, and the resulting mixture was refluxed overnight. Water (200 mL) and EtOAc (500 mL) were added. The aqueous layer was separated and extracted with EtOAc (2×500 mL), and the combined extracts dried over Na2SO4. The solvent was evaporated at reduced pressure and the crude product purified by column chromatography (20% EtOAc in hexanes) to give 9 g (91%) of the biphenyl intermediate 89 as a yellow solid.

Workup

  1. additionwere mixed under a rapid flow of argon
  2. temperaturethe resulting mixture was refluxed overnight
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc (2×500 mL)
  5. dry with materialthe combined extracts dried over Na2SO4
  6. customThe solvent was evaporated at reduced pressure
  7. customthe crude product purified by column chromatography (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-37b21ccea4d740cb8026f63697545f83
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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