N-bromobutanimide → 5-Bromo-4-fluoro-2-methoxy-benzonitrile
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1.C1C(=O)N([Br:19])C(=O)C1>C(O)(C(F)(F)F)=O>[Br:19][C:9]1[C:2]([F:1])=[CH:3][C:4]([O:10][CH3:11])=[C:5]([CH:8]=1)[C:6]#[N:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a 500 mL flask was added 4-fluoro-2-methoxybenzonitrile (9.00 g, 59.5 mmol), NBS (12.7 g, 71.5 mmol) and TFA (40 mL); the resulting mixture was stirred for 4 h at 65° C. Analysis of the reaction by LC indicated completion of the reaction. The reaction mixture was concentrated to dryness, treated with EtOAc (200 mL) and washed with brine and water, dried (Na2SO4), filtered and concentrated to dryness. The resulting organic residue was purified by MPLC with the solvent systems of hexanes/EtOAc=1/1 to furnish the desired product: LC/MS: [(M+2)]+=232;
Workup
- customAnalysis of the reaction by LC
- customcompletion of the reaction
- concentrationThe reaction mixture was concentrated to dryness
- additiontreated with EtOAc (200 mL)
- washwashed with brine and water
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe resulting organic residue was purified by MPLC with the solvent systems of hexanes/EtOAc=1/1
Sources & evidence
- ORD record
- ord-5ae139a9bf7c4a72bb4fdff4699e07e9
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206199B2
Reaction notes
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