Dimethylformamide → 5-Bromo-2-(2,2,2-trifluoroethoxy)pyridine

HRID 1385869Notes

Reaction equation

HRID 1385869 reaction equation
[H-].[Na+].CN(C=O)C.[CH2:8]([OH:13])[C:9]([F:12])([F:11])[F:10].Br[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1>O>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([O:13][CH2:8][C:9]([F:12])([F:11])[F:10])=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 223919645-Bromo-2-(2,2,2-trifluoroethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydride (18.6 g, 60%, 464 mmol) was introduced into DMF (500 ml) under nitrogen. Trifluoroethanol (32.2 ml, 443 mmol) was added dropwise at 10° C. After 1 hour, 2,5-dibromopyridine (100 g, 422 mmol) was added portionwise, and the mixture was stirred in a water bath for 24 hours at 20° C. It was then stirred with water and extracted with heptane/ethyl acetate 9:1. Distillation of the crude product (105 g) yielded 5-bromo-2-trifluoroethoxypyridine, 82.1 g (purity 93%), colorless fluid, b.p. 97-104° C. at 18 mbar.

Workup

  1. extractionextracted with heptane/ethyl acetate 9:1
  2. distillationDistillation of the crude product (105 g)

Sources & evidence

ORD record
ord-c3904f075860431aaeb8779654c727d2
Source dataset
uspto-grants-2001_07
Patent number
US06265350B1

Reaction notes

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