4-Acetylpyridine → 4-(Bromoacetyl)pyridine hydrobromide
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:10]Br>Br>[BrH:10].[Br:10][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
4-Acetylpyridine (10 g) was combined with 48% hydrogen bromide solution (18 ml) and heated to 70° C. Bromine (4.7 ml) dissolved in 48% hydrogen bromide solution (5 ml) was then added dropwise and heating then continued for 2.5 h. The precipitate which had formed was collected by filtration, washed with 1:1 methanol:hexane (20 ml) and dried to give a cream solid (19.5 g) as a 2:1 mixture of product:starting material by 1H nmr.
Workup
- additionwas then added dropwise
- temperatureheating
- customThe precipitate which had formed
- filtrationwas collected by filtration
- washwashed with 1:1 methanol
- dry with materialhexane (20 ml) and dried
Sources & evidence
- ORD record
- ord-bdc6eab8bafd4ce3b537e71ed099ffcf
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05972936
Reaction notes
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