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

HRID 1976052Notes

Reaction equation

HRID 1976052 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].Cl[C:10]1[C:15]([Br:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][N:11]=1.O>O1CCCC1>[Br:16][C:15]1[C:10]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[N:11][CH:12]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:14]=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 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
22 °C

Procedure

To 2,2,2-trifluoroethanol (1.4 ml 19.2 mmol) in tetrahydrofuran (3 ml) was added sodium hydride (760 mg, 60% suspension in oil, 19.0 mmol) and the suspension was stirred at 22° C. for 20 mins. 2-Chloro-3-bromo-5-trifluoromethylpyridine (1.0 g, 3.84 mmol) in tetrahydrofuran (2 ml) was then added and the mixture stirred for 16 hrs at 22° C., before being poured into water (100 ml) and extracted with ethyl acetate (2×100 ml). The extracts were dried (MgSO4) and concentrated to give the product as an oil (776 mg, 62% yield).

Workup

  1. stirringthe mixture stirred for 16 hrs at 22° C.
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. dry with materialThe extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0f5073e8b08f40c1ae1ce29e4cada108
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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