Water → 3-Bromo-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)pyridine

HRID 1976061Notes

Reaction equation

HRID 1976061 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].[Br:9][C:10]1[C:11](Cl)=[N:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.O>O1CCCC1>[Br:9][C:10]1[C:11]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[N:12][CH:13]=[C:14]([C:16]([F:18])([F:17])[F:19])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 135360613-Bromo-2-chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 220002003-Bromo-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)pyridineYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2,2,2-trifluoroethanol (1.4 mL, 19.2 mmol) in tetrahydrofuran (3 mL) was added sodium hydride (60% suspension in oil, 760 mg, 19.0 mmol) and the suspension formed was stirred for 20 minutes. 3-Bromo-2-chloro-5-trifluoromethylpyridine (1.0 g, 3.84 mmol) was then added and the solution stirred at room temperature for 16 hrs. Water (100 mL) was added and the mixture formed was extracted with ethyl acetate (2×100 mL). The extracts were dried (MgSO4) and concentrated to give the product as an oil (776 mg, 2.4 mmol, 62% yield).

Workup

  1. customthe suspension formed
  2. stirringthe solution stirred at room temperature for 16 hrs
  3. customthe mixture formed
  4. extractionwas extracted with ethyl acetate (2×100 mL)
  5. dry with materialThe extracts were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-28913db90a0d4f64a818599b0b9536e3
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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