反应 #2320133

ord-f756173202da4418ae19d937d2040ba8

反应方程式

OB(O)c1ccc(Br)cc1
4-bromophenylboronic acid
Cc1ccc(Br)nc1
2-bromo-5-methylpyridine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COCCOC
1,2-dimethoxyethane
Cc1ccc(-c2ccc(Br)cc2)nc1
2-(4-bromophenyl)-5-methylpyridine
收率 91.9%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度The mixture was heated
  2. 2
    温度to reflux under nitrogen atmosphere for 18 hours
  3. 3
    温度After the reaction was cooled down
  4. 4
    其他The mixture was separated in a separatory funnel
  5. 5
    其他The organic phases were collected
  6. 6
    其他evaporated
  7. 7
    workup.DISTILLATIONThe mixture was distilled

实验过程

To a 500 mL round bottom flask, 4-bromophenylboronic acid (25.0 g, 0.125), 2-bromo-5-methylpyridine (20.0 g, 0.114 mol), palladium(0)tetrakistriphenylphosphine (4.0 g, 0.0035 mol), potassium carbonate (47.0 g, 0.34 mol.), 1,2-dimethoxyethane (120 mL) and water (120 mL.) were added. The mixture was heated to reflux under nitrogen atmosphere for 18 hours. After the reaction was cooled down, 100 mL of water and 150 mL of ethyl acetate were added. The mixture was separated in a separatory funnel. The organic phases were collected, combined and evaporated. The mixture was distilled using a kugelrohred (spelling?) to obtain 2-(4-bromophenyl)-5-methylpyridine (26.0 g) as a white solid that was further purified by recrystallization in hexanes.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07709100B2uspto-grants-2010_05