2,5-Dibromopyridine → 5-Bromo-2-(methylthio)pyridine
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][S-:10].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([S:10][CH3:9])=[N:3][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
A mixture of 2,5-dibromopyridine (7) (1100 g, 4.64 mol), tetrabutylammonium bromide (55 g, 0.037 equivalent) and a 15% aqueous sodium thiomethoxide solution (2387 g, 1.1 equivalent) was heated at 85 to 90° C. for 3.5 hours. After the reaction mixture was cooled to 10° C., the resulting solid was filtered off. The organic layer was washed with cold water (1 L) and concentrated to obtain the crude product (8) (985 g, yield 104%). The crude product (8) (908 g) was purified by recrystallization using 2-propanol (2.1 L) and water (4.2 L) to obtain a compound (8) as crystals (831 g, yield 91.5%).
Workup
- filtrationthe resulting solid was filtered off
- washThe organic layer was washed with cold water (1 L)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-be358d7e0dc542189aede10bb6039ed0
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06765096B1
Reaction notes
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