N-bromobutanimide → 3-Bromo-2-chloro-6-fluorobenzonitrile
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].C1C(=O)N([Br:18])C(=O)C1>OS(C(F)(F)F)(=O)=O>[Br:18][C:9]1[C:2]([Cl:1])=[C:3]([C:6]([F:10])=[CH:7][CH:8]=1)[C:4]#[N:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Chloro-6-fluorobenzonitrile (15.6 g, 100 mmol) was dissolved in triflic acid (75 mL) at 0° C., then NBS (17.8 g, 100 mmol) was added. The reaction was warmed up to room temperature and stirred overnight. The reaction mixture was poured into ice and extracted with DCM (2×). DCM layers were washed with NaHCO3 and brine. The DCM was dried over Na2SO4 then filtered and concentrated. The product was purified by chromatography through a 330 g ISCO Redi-Sep column with 10-20% ethyl acetate/hexane solvent system to yield 3-bromo-2-chloro-6-fluorobenzonitrile.
Workup
- additionThe reaction mixture was poured into ice
- extractionextracted with DCM (2×)
- washDCM layers were washed with NaHCO3 and brine
- dry with materialThe DCM was dried over Na2SO4
- filtrationthen filtered
- concentrationconcentrated
- customThe product was purified by chromatography through a 330 g ISCO Redi-Sep column with 10-20% ethyl acetate/hexane solvent system
Sources & evidence
- ORD record
- ord-01a8dcf545634e22ad91bb6a890da91e
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206199B2
Reaction notes
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