Allyl bromide → HCID 15322740, compound

HRID 1594896Notes

Reaction equation

HRID 1594896 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[Li+].[CH3:10][CH:11]([N-]C(C)C)[CH3:12].C(Br)C=C.[NH4+].[Cl-]>C1COCC1>[CH2:12]([C:7]1[C:6]([Br:8])=[CH:5][N:4]=[CH:3][C:2]=1[Br:1])[CH:11]=[CH2:10]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 693693,5-DibromopyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 15322740HCID 15322740, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A THF (100 mL) solution of 3,5-dibromopyridine (5 g, 21.1 mmol) at −78° C. was added via cannula to a solution of LDA (22.2 mmol) in THF (700 mL) at −78° C. keeping the temperature <60° C. After stirring for 10 min. at −78° C., allyl bromide (2.56 mL, 29.5 mmol) was added via syringe and the reaction mixture was stirred for 2 hr at −78° C. Saturated NH4Cl (100 mL) was added slowly to quench the reaction. The organic layer was separated, washed with brine and dried (MgSO4). Filtration and concentration in vacuo gave the title compound as an oil which was purified by chromatography on silica gel with hexane:ethyl acetate 9:1.

Workup

  1. customthe temperature <60° C
  2. stirringthe reaction mixture was stirred for 2 hr at −78° C
  3. customto quench
  4. customthe reaction
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-a970f891a23745fcb11bfeb060c23129
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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