Tetrahydrofuran → HCID 66667735, compound

HRID 512076Notes

Reaction equation

HRID 512076 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]=[C:17]([C:19]([F:22])([F:21])[F:20])[C:16]([Cl:23])=[CH:15][N:14]=1.[O:24]1CCCC1>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:24][C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[C:16]([Cl:23])=[CH:15][N:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 269860162,5-Dichloro-4-(trifluoromethyl)pyridine

Product 1

HCID 66667735HCID 66667735, compoundYield 71%

Procedure

To a solution of 4-bromobenzylbromide (0.43 g, 2.3 mmol) in tetrahydrofuran (8 mL) at 0° C. was added sodium hydride (60% w/w dispersion in oil; 138 mg, 3.45 mmol). The mixture was stirred for 1 hour at room temperature, then 2,5-dichloro-4-trifluoromethylpyridine (0.5 g, 2.3 mmol) was added in one portion and the reaction heated under reflux for 4 hours. The reaction mixture was cooled and partitioned between ethyl acetate (30 mL) and water (10 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo to give the crude title compound (0.61 g, 71%). This was used without further purification.

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned between ethyl acetate (30 mL) and 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-5a942bbecdbc47e6864c8f875e64d4a1
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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