Benzophenone → HCID 10830973, compound

HRID 1037648Notes

Reaction equation

HRID 1037648 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[N:8]=1.[C:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[Br:13][C:9]1[N:8]=[C:7]([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[OH:21])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 122742,6-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 10830973HCID 10830973, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C. a 2.5 M solution of n-butyl lithium in hexanes (18.6 mL, 46.4 mmol, 1.1 equiv) was added dropwise to 2,6-dibromopyridine (1) (10.0 g, 42.2 mmol, 1.0 equiv) in THF (780 mL). The solution was then stirred for 20 min at which point benzophenone (8.07 g, 44.3 mmol, 1.05 equiv) was added. The reaction was allowed to stir an additional 0.5 hr at −78° C., at this time the cooling bath was removed and the reaction allowed to warm room temperature. The reaction was stirred at room temperature for 1 hr and quenched with saturated sodium bicarbonate (250 mL). The layers were separated and the aqueous layer extracted with dichloromethane (250 mL). The combined organic layers were dried over sodium sulfate and absorbed onto silica gel (30 g) by concentration under reduced pressure. This material was then purified on a silica gel column (300 g) by eluting with heptanes (2 L), ethyl acetate (2%) in heptanes (2 L) and finally ethyl acetate (5%) in heptanes (2 L). The desired product was isolated pure in 35% yield (5.0 g). A second fraction (5.4 g) of product and benzophenone was also isolated.

Workup

  1. additionwas added
  2. customwas removed
  3. temperatureto warm room temperature
  4. stirringThe reaction was stirred at room temperature for 1 hr
  5. customquenched with saturated sodium bicarbonate (250 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted with dichloromethane (250 mL)
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. customabsorbed onto silica gel (30 g) by concentration under reduced pressure
  10. customThis material was then purified on a silica gel column (300 g)
  11. washby eluting with heptanes (2 L), ethyl acetate (2%) in heptanes (2 L) and finally ethyl acetate (5%) in heptanes (2 L)

Sources & evidence

ORD record
ord-f1bd899a30444c98a7c23d57826b8c1f
Source dataset
uspto-grants-2013_10
Patent number
US08546501B2

Reaction notes

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