Acetophenone → HCID 86652883, compound

HRID 1037652Notes

Reaction equation

HRID 1037652 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:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])[CH3:15]>C1COCC1>[Br:13][C:9]1[N:8]=[C:7]([C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:16])[CH3:15])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 122742,6-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 86652883HCID 86652883, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C. a 2.5 M solution of n-butyl lithium (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 acetophenone (5.06 g, 44.3 mmol, 1.0 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 purifies on a silica gel column (300 g) by eluting with heptanes (1 L), ethyl acetate (2%) in heptanes (2 L), ethyl acetate (5%) in heptanes (2 L) and finally ethyl acetate (10%) in heptanes (1 L). The desired product was isolated pure in 40% yield (4.7 g).

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. washby eluting with heptanes (1 L), ethyl acetate (2%) in heptanes (2 L), ethyl acetate (5%) in heptanes (2 L)

Sources & evidence

ORD record
ord-552c150b10f14725b784efc3758f9fcf
Source dataset
uspto-grants-2013_10
Patent number
US08546501B2

Reaction notes

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