Potassium Hydroxide → 3-Bromo-5-ethynylpyridine

HRID 606804Notes

Reaction equation

HRID 606804 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:10]#[C:11][Si](C)(C)C)[CH:9]=1>CO>[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:10]#[CH:11])[CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 665244243-Bromo-5-((trimethylsilyl)ethynyl)pyridine

Product 1

HCID 154238793-Bromo-5-ethynylpyridineYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add a 1 M aqueous solution of potassium hydroxide (369.7 mmol, 370 mL) to a stirred solution of 3-bromo-5-trimethylsilanylethynyl-pyridine (85.4 g, 336.1 mmol), (prepared essentially as described in PREPARATION 22), in 850 mL of methanol at 15° C. Stir at room temperature for 2 h and concentrate. Dissolve the residue in 800 mL of dichloromethane, sequentially wash with water (160 mL) and an aqueous saturated solution of sodium chloride (160 mL), dry (magnesium sulfate) and concentrate with only slight heating to give the title compound as a pale volatile brown solid (53.84 g, 88%).

Workup

  1. custom(prepared essentially
  2. concentrationconcentrate
  3. dissolutionDissolve the residue in 800 mL of dichloromethane
  4. washsequentially wash with water (160 mL)
  5. dry with materialan aqueous saturated solution of sodium chloride (160 mL), dry (magnesium sulfate)
  6. concentrationconcentrate
  7. temperaturewith only slight heating

Sources & evidence

ORD record
ord-a9a4647a6bef4345bf1c866e9a96a3ee
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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