N-bromobutanimide → 2-Amino-5-bromobenzonitrile
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C1C(=O)N([Br:17])C(=O)C1>ClCCl>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:17])=[CH:6][C:3]=1[C:4]#[N:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Aminobenzonitrile (5.0 g, 42.3 mmol) was taken into dichloromethane (60 mL). NBS (7.54 g, 42.3 mmol) was added and stirred at 0° C. for 3 h. The reaction mixture was diluted with dichloromethane and washed with brine, dried over MgSO4. The crude product was purified by column chromatography (hexane/ethyl acetate=10/1) to afford the titled compound (7.20 g, 87%). 1HNMR (400 MHz, DMSO-d6): δ 6.22 (s, 2H), 6.75 (d, J=9.2 Hz, 1H), 7.42 (dd, J=8.8 Hz, 2.4 Hz, 1H), 7.58 (s, 1H).
Workup
- washwashed with brine
- dry with materialdried over MgSO4
- customThe crude product was purified by column chromatography (hexane/ethyl acetate=10/1)
Sources & evidence
- ORD record
- ord-c219501fc3cb4304b23f8d7cf37f207d
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461157B2
Reaction notes
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