Water → 5-Bromo-4-cyano-2-hydroxy-3-methylbenzoic acid
Reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([OH:12])[C:4]=1[CH3:13])#[N:2].[Br:14]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:14][C:11]1[C:3]([C:1]#[N:2])=[C:4]([CH3:13])[C:5]([OH:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
To a solution of 4-cyano-2-hydroxy-3-methylbenzoic acid (5.50 g) in DMF (50.0 mL) was added N-bromosuccinimide (5.50 g) under ice-cooling, and the mixture was stirred at 15° C. for 16 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (7.40 g: containing DMF).
Workup
- temperaturecooling
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b27072acd1334e41b4b306b4b704372e
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315458B2
Reaction notes
Loading…