Water → 3-(Diethylboryl)pyridine

HRID 429382Notes

Reaction equation

HRID 429382 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH2:13]([B:15]([CH2:18][CH3:19])OC)[CH3:14].O>C(OCCCC)CCC.[Cl-].[Na+].O>[CH2:13]([B:15]([CH2:18][CH3:19])[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 122863-BromopyridineHCID 522516DiethylmethoxyboraneHCID 178418339Butyllithium

Product 1

HCID 6428513-(Diethylboryl)pyridineYield 76.8%

Reagents, catalysts & solvents 2

HCID 8909Butyl etherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Into a solution of n-butyl lithium (165 ml, 264 mmol) in butyl ether (250 ml) at −78 degrees under nitrogen was added 3-bromopyridine (25.4 ml, 264 mmol). After 1 h, added diethylmethoxyborane (52 ml, 396 mmol). The mixture was allowed to warm to room temperature. After 16 h, added water and brine, separated organic layer, dried over sodium sulfate, then concentrated. The resulting slurry was dissolved in isopropanol (500 ml), cooled and the product isolated by filtration give diethyl(3-pyridyl)borane (29.8 g).

Workup

  1. waitAfter 16 h
  2. customseparated organic layer
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe resulting slurry was dissolved in isopropanol (500 ml)
  6. temperaturecooled
  7. customthe product isolated by filtration

Sources & evidence

ORD record
ord-49831452b1514267bb7193666617d77f
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

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