5-Bromo-3-pyridinecarboxaldehyde → 3-Bromo-5-vinylpyridine

HRID 593583Notes

Reaction equation

HRID 593583 reaction equation
[Br-].[CH3:2]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si](C)(C)N[Si](C)(C)C.[Na].[Br:32][C:33]1[CH:34]=[C:35]([CH:39]=O)[CH:36]=[N:37][CH:38]=1>O1CCCC1>[Br:32][C:33]1[CH:38]=[N:37][CH:36]=[C:35]([CH:39]=[CH2:2])[CH:34]=1

Participants

5

Reactant 3

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 45051731Sodium hexamethyidisilazaneHCID 178503020HCID 178503020, compound

Product 1

HCID 234363373-Bromo-5-vinylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyltriphenylphosphine bromide (3.16 g, 8.87 mmol) in tetrahydrofuran (20 mL) is added sodium hexamethyldisilazane (1M solution in THF, 9.67 mL, 9.67 mmol) dropwise. The reaction mixture is stirred at room temperature for 30 min, whereupon 5-bromo-pyridine-3-carbaldehyde (1.5 g, 8.06 mmol) is added. The reaction mixture is allowed to stir at room temperature for 1 h. The mixture is concentrated and the residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 7:3) to afford 3-bromo-5-vinyl-pyridine as a colorless oil. MS (ESI) m/z 185.91 (M+H)+.

Workup

  1. additionis added
  2. concentrationThe mixture is concentrated
  3. customthe residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-d75969a0a89e484e81f163570b97c08b
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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