Potassium Hydroxide → 3-Bromo-5-ethynylpyridine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- custom(prepared essentially
- concentrationconcentrate
- dissolutionDissolve the residue in 800 mL of dichloromethane
- washsequentially wash with water (160 mL)
- dry with materialan aqueous saturated solution of sodium chloride (160 mL), dry (magnesium sulfate)
- concentrationconcentrate
- 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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