Water → HCID 70096444, compound

HRID 868989Notes

Reaction equation

HRID 868989 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:9]2[O:13][CH2:12][CH2:11][O:10]2)[N:5]([CH3:8])[C:6]=1Br.[Li]CCCC.O>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]([CH:9]2[O:13][CH2:12][CH2:11][O:10]2)[N:5]([CH3:8])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70114232HCID 70114232, compoundHCID 178418339Butyllithium

Product 1

HCID 70096444HCID 70096444, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,5-dibromo-2-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazole (1 g, 3.2 mmol) in dry THF (20 mL) was added n-BuLi (2.5 M in hexane, 1.28 mL, 3.2 mmol) dropwise at −68° C. over 30 min. The reaction mixture was stirred at the same temperature for 2 h and then was allowed to warm to r.t. over 1 h. 10 mL of water was added slowly at 0° C. to quench the reaction. The residue was extracted with EtOAc (50 mL×2) and the combined organic layers were washed with water (20 mL) and brine (20 mL), dried, and concentrated to give a yellow oil (678 mg). MS (ESI): m/z 233 [M+H]+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe residue was extracted with EtOAc (50 mL×2)
  4. washthe combined organic layers were washed with water (20 mL) and brine (20 mL)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-28d4f50f456a416485ebcc68026569a9
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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