2-Bromopyridine → HCID 53446408, compound

HRID 443047Notes

Reaction equation

HRID 443047 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:1][C:8]#[N:9]

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 8794PhenylacetonitrileHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 53446408HCID 53446408, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of benzylcyanide (12.33 g) in tetrahydrofuran (85 ml) was added dropwise, at -70° C. in argon streams, a hexane solution (65 ml) of n-butyl lithium. The mixture was then stirred for 30 minutes at -50° C., to which was then added dropwise 2-bromopyridine (9.7 ml). The reaction temperature was gradually raised up to 0° C. Fifteen minutes later, a saturated ammonium chloride solution was added to the reaction mixture, which was subjected to extraction with ethyl acetate. The extract solution was washed with water, dried over anhydrous sodium sulfate and concentrated to dryness. The concentrate was purified by means of a silica gel column chromatography to give the title compound (6.59 g).

Workup

  1. temperatureThe reaction temperature was gradually raised up to 0° C
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe extract solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe concentrate was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-f495bc62fed24094a1ec36b14c48b60f
Source dataset
uspto-grants-1999_04
Patent number
US05891916

Reaction notes

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