Potassium Carbonate → HCID 58020026, compound

HRID 1632060Notes

Reaction equation

HRID 1632060 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCO.O.COCCOC>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11457Benzene, 1-bromo-3-nitro-HCID 11776TriphenylphosphineHCID 2734343(2,6-Dimethoxyphenyl)boronic acid

Product 1

HCID 58020026HCID 58020026, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To 1-bromo-3-nitrobenzene (2.02 g, 10.0 mmol), 2,6-dimethoxyphenylboronic acid (2.70 g, 15.0 mmol), triphenylphosphine (0.52 g, 2.0 mmol), K2CO3 (4.14 g, 30.0 mmol) and palladium(II) acetate (0.009 g, 0.04 mmol) was added DME (80 mL) and EtOH/H2O (1:1, 20 mL). Argon gas was bubbled through the stirred reaction for 5 min. The reaction was stirred at 80° C. under argon for 20 h. The reaction was cooled to room temperature, concentrated, and H2O (60 mL) and dichloromethane (80 mL) were added. The layers were separated and the aqueous was extracted with dichloromethane (2×40 mL). The combined organic extracts were dried with Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography using 10% ethyl acetate/hexanes as eluent to afford 1.69 g (65%) of I-81 as a white solid.

Workup

  1. customArgon gas was bubbled through the stirred reaction for 5 min
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated
  4. additionH2O (60 mL) and dichloromethane (80 mL) were added
  5. customThe layers were separated
  6. extractionthe aqueous was extracted with dichloromethane (2×40 mL)
  7. dry with materialThe combined organic extracts were dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography
  11. customto afford 1.69 g (65%) of I-81 as a white solid

Sources & evidence

ORD record
ord-7311a0c255fb4e3293d3d891e5718195
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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