2,2,2-Trifluoroethanol → 5-Bromo-2-(2,2,2-trifluoroethoxy)pyrimidine

HRID 1187780Notes

Reaction equation

HRID 1187780 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].Br[C:10]1[N:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1>CN(C=O)C>[Br:16][C:13]1[CH:12]=[N:11][C:10]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 109555882,5-Dibromopyrimidine

Product 1

HCID 179595455-Bromo-2-(2,2,2-trifluoroethoxy)pyrimidineYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To sodium hydride (303 mg) under an argon atmosphere at 0° C. was added dropwise 2,2,2-trifluoroethanol (775 μl) and the mixture was then stirred at RT for 90 min. A solution of 2,5-dibromopyrimidine (1.5 g) in DMF (8 ml) was then added and stirring continued at RT for 2 hours. The reaction mixture was poured into ice (50 mL) and extracted with EtOAc (2×50 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to afford 5-bromo-2-(2,2,2-trifluoro-ethoxy)-pyrimidine (790 mg, 49%) as a yellow oil which was used in the next step without further purification. MS (EI): 258 ([{81Br}M]+), 256 ([{79Br}M]+), 189 ([{81Br}M−CF3]+), 187 ([{79Br}M−CF3]+).

Workup

  1. stirringstirring
  2. waitcontinued at RT for 2 hours
  3. extractionextracted with EtOAc (2×50 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63c081562fa142f0ae48f1fbf3231247
Source dataset
uspto-grants-2014_03
Patent number
US08673950B2

Reaction notes

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