Hydrochloric Acid → 2-Acetyl-6-bromopyridine

HRID 423176Notes

Reaction equation

HRID 423176 reaction equation
[Li]CCCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[N:14]=1.Cl.[CH3:21][CH2:22][O:23]CC>CN(C)C(=O)C>[Br:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:22](=[O:23])[CH3:21])[N:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8058HexaneHCID 122742,6-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 112985782-Acetyl-6-bromopyridineYield 28%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

12.5 mL of a solution of n-BuLi 1.6 M in hexane (20 mmol) are added at −78° C. to a solution of 4.70 g 2,6-dibromopyridine 20 (20 mmol) in 100 mL anhydrous ether. The reaction medium is left in the cold for 30 min. 2 mL N,N-dimethylacetamide are added cold (−78° C.) for 1 h, then allowed to reach the ambient temperature. The reaction medium is neutralized with 25 mL of an aqueous HCl 1M solution. The aqueous phase is extracted with Et2O (3×20 mL). The combined organic phases are washed with brine (3×20 mL), dried on MgSO4, filtered, then evaporated under vacuum. The raw product is recrystallized in an Et2O/n-C5H12 (1/2) mixture. 1.18 g of an orange solid is obtained, i.e. a 28% yield.

Workup

  1. customthe ambient temperature
  2. extractionThe aqueous phase is extracted with Et2O (3×20 mL)
  3. washThe combined organic phases are washed with brine (3×20 mL)
  4. customdried on MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe raw product is recrystallized in an Et2O/n-C5H12 (1/2) mixture

Sources & evidence

ORD record
ord-049a92dfcdd94d53bbfd9359e543b8e2
Source dataset
uspto-grants-2012_01
Patent number
US08101762B2

Reaction notes

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