1,4-Dibromobenzene → HCID 11367805, compound

HRID 422120Notes

Reaction equation

HRID 422120 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)CCC>O>[O:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[C:2]1[CH:7]=[CH:6][C:5]([C:16]2[O:15][CH:14]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78041,4-DibromobenzeneHCID 43936882-(Tributylstannyl)furan

Product 1

HCID 11367805HCID 11367805, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 1,4-dibromobenzene (5 mmol) was added palladium tetrakis-triphenylphosphine (400 mg). The reaction mixture was kept stirring for 15 min after which 2-tributylstannylfuran (10 mmol) was added and the reaction mixture was refluxed at 100° C. for 24 h. The solvent was then evaporated to dryness to give a dark brown residue that was suspended in water and extracted with CH2Cl2. The organic layer was passed over hyflo, dried (Na2SO4) and evaporated to dryness under reduced pressure to give 15 in 91% yield; mp 149-150° C. 1H NMR (DMSO-d6); δ 6.62 (d, 2H), 7.01 (d, 2H), 7.76-7.79 (m, 6H). MS (ESI) m/e (rel. int.): 210 (M+, 100), 181 (40), 153 (30). Anal. Calc. for C14H10O2: C %, 79.98; H %, 4.79. Found C %, 80.12; H %, 4.59.

Workup

  1. additionwas added
  2. customThe solvent was then evaporated to dryness
  3. customto give a dark brown residue that
  4. extractionextracted with CH2Cl2
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f7e976609b4a4cfdb33ddd4ed99aef86
Source dataset
uspto-grants-2012_01
Patent number
US08101636B2

Reaction notes

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