Water → 3-(Diethylboryl)pyridine

HRID 489857Notes

Reaction equation

HRID 489857 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-b6a8a44ae13a4ce7be9edab8f62c957f
Source dataset
uspto-grants-2005_12
Patent number
US06979693B2

Reaction notes

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