Sodium Carbonate → HCID 66876773, compound

HRID 1964067Notes

Reaction equation

HRID 1964067 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:7])[O:5][CH:6]=1.[NH2:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>[CH3:7][C:4]1[O:5][CH:6]=[C:2]([C:13]2[CH:14]=[C:9]([CH:10]=[CH:11][CH:12]=2)[NH2:8])[CH:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 922693-Aminophenylboronic acidHCID 1112656424666-43-1

Product 1

HCID 66876773HCID 66876773, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

500 mg (3.1 mmol) of 4-bromo-2-methylfuran was dissolved in 12 mL of toluene, and then 3 mL of methanol, 638 mg (4.7 mmol) of m-aminophenyl boronic acid, and 3 mL of 2M aqueous sodium carbonate solution were added thereto. Subsequently, 180 mg (0.16 mmol) of triphenylphosphine palladium was added, and the mixture was stirred at 100° C. for 17 hours. After cooling, anhydrous magnesium sulfate was added to the mixture, and the mixture was stirred. Filtration was then conducted, and the filtrate was condensed. The resulting product was separated and purified using silica gel column chromatography to give 3-(5-methylfuran-3-yl)aniline (yield: 52%).

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture was stirred
  3. filtrationFiltration
  4. customcondensed
  5. customThe resulting product was separated
  6. custompurified

Sources & evidence

ORD record
ord-80a5442df0484ea699569bdaa356fde2
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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