Water → 3-Bromobenzamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[OH2:10]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([NH2:6])=[O:10]Participants
4
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 3-bromobenzonitrile (0.91 g, 5 mmol) in dioxane (19 mL), NaBO3.4H2O (2.12 g, 13.78 mmol) and H2O (19 mL) were added. The mixture was stirred at 80° C. 16 hours (h), cooled, added of H2O and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and evaporated. Purification of the residue by column chromatography (hexane/EtOAc 2:8) and recrystallization gave the desired product as colorless tablets. Yield 80% (EtOH). Mp: 156–7° C. (lit. 156° C.) (Pearson, D. E. et al., J. Org. Chem., 28: 3147–3149, (1963)). MS (EI): m/z 199 (M+); 183 (100%).
Workup
- temperature16 hours (h), cooled
- extractionextracted with CH2Cl2
- dry with materialThe combined organic layers were dried over Na2SO4
- customevaporated
- customPurification of the residue
- customby column chromatography (hexane/EtOAc 2:8) and recrystallization
Sources & evidence
- ORD record
- ord-e1cdeceb7dc34f52869aa74648684cc2
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07176201B2
Reaction notes
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