Methyl 2-(4-bromophenyl)acetate → Methyl (4-cyanophenyl)acetate
Reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1>CN1C(=O)CCC1>[C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)#[N:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
5.1 g (56.7 mmol) of copper(I) cyanide were added to a solution of 10 g (43.7 mmol) of methyl 4-bromophenylacetate in 44 ml of NMP, and, in a microwave oven, the mixture was then heated to 200° C. for 60 min. The reaction mixture was then purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 5:1). This gave 4.65 g (61% of theory) of the title compound.
Workup
- customThe reaction mixture was then purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 5:1)
Sources & evidence
- ORD record
- ord-5781a4ae8ef74f1a9b9440ff53910401
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018258B2
Reaction notes
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