Tetrahydrofuran → HCID 66667687, compound

HRID 512077Notes

Reaction equation

HRID 512077 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=1.[O:20]1CCCC1>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:20][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 276852,5-DichloropyridineHCID 685274-Bromobenzyl bromide

Product 1

HCID 66667687HCID 66667687, compoundYield 76%

Procedure

To a solution of 4-bromobenzylbromide (1.26 g, 6.7 mmol) in tetrahydrofuran (10 mL) at 0° C. was added a sodium hydride (60% w/w dispersion in oil; 0.40 g, 10 mmol). The mixture was stirred for 1 hour at room temperature, then 2,5-dichloro pyridine (1 g, 6.7 mmol) was added in one portion and the reaction mixture was heated under reflux overnight. TLC The reaction mixture was cooled and partitioned between ethyl acetate (40 mL) and cold water (10 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo to give the crude title compound (1.54 g, 76%). This was used without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. temperatureTLC The reaction mixture was cooled
  4. custompartitioned between ethyl acetate (40 mL) and cold water (10 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f7109c9734d445e9b3ab81bc99c40143
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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