2,3-Dibromopropene → HCID 86631523, compound

HRID 335223Notes

Reaction equation

HRID 335223 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].C([N-]C(C)C)(C)C.[Li+].[Br:16][C:17]([CH2:19]Br)=[CH2:18]>C1COCC1>[Br:16][C:17](=[CH2:18])[CH2:19][CH:4]1[CH2:5][CH2:6][N:2]([CH3:1])[C:3]1=[O:7]

Participants

5

Reactant 3

HCID 105522,3-DibromopropeneHCID 13387N-methyl-2-pyrrolidoneHCID 2724682Lithium diisopropylamide

Product 1

HCID 86631523HCID 86631523, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1-Methyl-2-pyrrolidinone (3.87 mL, 40.3 mmol) was combined with 25 mL of THF and cooled to −78° C. Lithium diisopropylamide (26.9 mL, 40.3 mmol) (1.5M in THF) was added slowly and the mixture was agitated for 30 minutes. 2,3-Dibromopropene (4.93 mL, 40.3 mmol) was added and the mixture was agitated overnight and allowed to warm up to ambient temperature. The reaction was quenched with sodium bicarbonate solution and extracted twice with ether. The extracts were washed with brine and evaporated. The crude product was purified by chromatography on silica gel, eluting with 30-50% ethyl acetate/hexane, to provide the title compound (5.01 g, 56.9% yield) as clear oil.

Workup

  1. stirringthe mixture was agitated overnight
  2. temperatureto warm up to ambient temperature
  3. customThe reaction was quenched with sodium bicarbonate solution
  4. extractionextracted twice with ether
  5. washThe extracts were washed with brine
  6. customevaporated
  7. customThe crude product was purified by chromatography on silica gel
  8. washeluting with 30-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-921ab06cc2eb41e4954607fafcff0719
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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