2,2,2-Trifluoroethanol → 3-Bromo-5-(2,2,2-trifluoroethoxy)pyridine

HRID 1642157Notes

Reaction equation

HRID 1642157 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](Br)[CH:13]=1>>[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[CH:13]=1

Participants

3

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 693693,5-Dibromopyridine

Product 1

HCID 225703523-Bromo-5-(2,2,2-trifluoroethoxy)pyridineYield 70%

Procedure

2,2,2-Trifluoroethanol and 3,5-dibromopyridine were processed as described in Example 7A except that the heating time was extended to 20 hours at 100° C. The reaction was quenched onto ice/water, extracted with ethyl ether, and concentrated. The residue was purified on silica gel (hexanes:ethyl acetate, 8:2) to provide the title compound as a colorless oil (70% yield). MS (DCI/NH3) m/z 256/258 (M+H)+.

Workup

  1. customThe reaction was quenched onto ice/water
  2. extractionextracted with ethyl ether
  3. concentrationconcentrated
  4. customThe residue was purified on silica gel (hexanes:ethyl acetate, 8:2)

Sources & evidence

ORD record
ord-5969c6dacaf14b2f92be22d6f01c349b
Source dataset
uspto-grants-2012_02
Patent number
US08119635B2

Reaction notes

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