Ethyl Acrylate → HCID 53973261, compound
Reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C([O-])(=O)C.[Na+]>[Pd].CN(C=O)C>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[CH:12]=[CH:11][C:10]([O:14][CH2:15][CH3:16])=[O:13])#[N:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 130 °C
Procedure
0.67 ml of the stock solution from Example 52, 3.05 g (16.8 mmols) of 2-bromobenzonitrile, 1.99 ml (18.4 mmols) of ethyl acrylate and 1.50 g (18.4 mmols) of anhydrous sodium acetate are added, under argon, to 16.3 ml of DMF, and the reaction mixture is stirred at 130° C. for 3 hours. After working up as described in Example 1, the crude product is recrystallised from a mixture of pentane and carbon tetrachloride. 1.5 g (7.5 mmols) of ethyl o-cyanocinnamate are obtained in the form of white crystals of melting point 56° C., corresponding to a yield of 44% of theory (conversion figure 4400; Pd content 0.01 mol %). Analysis for C12H11NO2 (molecular weight 201.23): calculated C 71.63; H 5.51; N 6.96; O 15.90, found C 71.17; H 5.64; N 6.88; O 16.56.
Workup
- customthe crude product is recrystallised from a mixture of pentane and carbon tetrachloride
Sources & evidence
- ORD record
- ord-d34ab9753d13471a8fbb446ecac07201
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04564479
Reaction notes
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