Toluene → 5-(2-Bromoethynyl)-2-methylpyridine

HRID 1400609Notes

Reaction equation

HRID 1400609 reaction equation
[Br:1][C:2](Br)=[CH:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>O>[Br:1][C:2]#[C:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 23665647Potassium tert-butoxideHCID 594551635-(2,2-Dibromovinyl)-2-methylpyridine

Product 1

HCID 120404695-(2-Bromoethynyl)-2-methylpyridineYield 32.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(2,2-dibromovinyl)-2-methylpyridine (0.10.9 g, 0.00393 mol), potassium tertbutoxide (0.88 g, 0.00787 mol) and toluene (13 mL) were heated at 80° C. for 4 h. After completion of reaction, the reaction mixture was cooled to RT, diluted with water (15 mL), and extracted with EtOAc (3×50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduce pressure to obtain product as a yellow oil (0.25 g, 32.4%).

Workup

  1. customAfter completion of reaction
  2. temperaturethe reaction mixture was cooled to RT
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa79c36261984a3e9aac9013499144c1
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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