Methyl 5-bromosalicylate → Methyl 5-cyano-2-hydroxybenzoate
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Cu](C#N)[C:14]#[N:15]>CN(C=O)C>[C:14]([C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A suspension of methyl 5-bromo-2-hydroxybenzoate (2 g, 8.66 mmol) and copper cyanide (1.861 g, 20.78 mmol) in DMF (30 ml) was stirred under nitrogen at 140° C. for 20 h. The reaction mixture was then cooled, quenched with water (120 ml) and extracted with ethyl acetate (3×80 ml). The organic phase was washed with saturated brine (50 ml), dried over sodium sulphate and evaporated in vacuo to yield the title compound as a white solid. 1 g.
Workup
- temperatureThe reaction mixture was then cooled
- customquenched with water (120 ml)
- extractionextracted with ethyl acetate (3×80 ml)
- washThe organic phase was washed with saturated brine (50 ml)
- dry with materialdried over sodium sulphate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-6cd28a0b631746ffb3178397f8960a2a
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
Loading…