1-Bromo-2-methyl-4-nitrobenzene → 2,5-Bis(2-methyl-4-nitrophenyl)furan

HRID 350702Notes

Reaction equation

HRID 350702 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].C([Sn](CCCC)(CCCC)[C:17]1[O:18][C:19]([Sn](CCCC)(CCCC)CCCC)=[CH:20][CH:21]=1)CCC>O1CCOCC1>[CH3:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:19]1[O:18][C:17]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[CH3:11])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 2516721-Bromo-2-methyl-4-nitrobenzeneHCID 115782772,5-Bis(tri-n-butylstannyl)furan

Product 1

HCID 107831862,5-Bis(2-methyl-4-nitrophenyl)furanYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-bromo-5-nitrotoluene (4.32 g, 20 mmol) and tetrakis (triphenylphospine) palladium (0) (0.40 g) in anhydrous 1,4-dioxane (50 ml) was added 2,5-bis (tri-n-butylstannyl) furan (6.46 g, 10 mmol) and the mixture was heated overnight under nitrogen at 95–100° C. The resulting orange suspension was diluted with hexanes (15 ml), cooled to room-temperature, and filtered to give, after rinsing with hexanes, an orange solid (3.10 g), mp 241–243° C. The product was recrystallized from DMF (100 ml) to give a bright orange fluffy solid (2.87 g, 85%), mp 242–243° C. 1H NMR (DMSO-d6): 2.69 (s, 6H), 7.31 (s, 2H), 8.12 (m, 4H), 8.23 (s, 2H). Anal. Calcd. for C18H14N2O5 (338.31): C, H, N.

Workup

  1. temperaturethe mixture was heated overnight under nitrogen at 95–100° C
  2. temperaturecooled to room-temperature
  3. filtrationfiltered
  4. customto give
  5. washafter rinsing with hexanes
  6. customThe product was recrystallized from DMF (100 ml)

Sources & evidence

ORD record
ord-51646b07bb86465ead476454f1046606
Source dataset
uspto-grants-2007_02
Patent number
US07183286B2

Reaction notes

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