Bromotrimethylsilane → 2-Bromo-4-(trifluoromethyl)pyridine

HRID 270565Notes

Reaction equation

HRID 270565 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[Br:12][Si](C)(C)C>C(#N)CC>[Br:12][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 1449582-Chloro-4-(trifluoromethyl)pyridine

Product 1

HCID 27815432-Bromo-4-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

A mixture of 2-chloro-4-(trifluoromethyl)pyridine (2.70 g, 14.9 mmol) and bromotrimethylsilane (3.90 mL, 29.6 mmol) in propanenitrile (15.0 mL) was heated under reflux for 22 h. The product (very volatile) was carefully rotary evaporated to give 4.07 g (propanenitrile contained) of thick light brown suspension w/o further purification. LC-MS calculated for C6H3BrF3N (M+H) 226.9; found 225.9/227.8.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 22 h
  3. customThe product (very volatile) was carefully rotary evaporated
  4. customto give
  5. custom4.07 g (propanenitrile contained) of thick light brown suspension w/o further purification

Sources & evidence

ORD record
ord-439b4ea4392d422dbbb8fd6c16404691
Source dataset
uspto-grants-2008_11
Patent number
US07449467B2

Reaction notes

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