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CAS No. : | 79432-87-4 | MDL No. : | MFCD00296965 |
Formula : | C10H9BrO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GPBINNSHRSTZQE-AATRIKPKSA-N |
M.W : | 241.08 | Pubchem ID : | 1482751 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; potassium carbonate;tetrakis(triphenylphosphine)palladium (0); In methanol; ethanol; toluene; | REFERENCE EXAMPLE 56 A suspension of methyl 3-bromocinnamate (3.8 g), phenyl borate (2.0 g), 1M potassium carbonate (20 ml) and ethanol (10 ml) in toluene(100 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.9 g), and the mixture was refluxed over night and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give colorless crystals (3.6 g), 1.8 g of which was dissolved in a solution of methanol (100 ml) and 1N sodium hydroxide (20 ml). The mixture was stirred at room temperature over night, concentrated, neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 3-phenylcinnamic acid (1.5 g) as colorless crystals. 1 H-NMR(delta ppm, CDCl3): 6.54 (1H, d, J=16.0 Hz), 7.39-7.67 (8H, m), 7.76-7.77 (1H,m), 7.87 (1H,d,J=16.0 Hz). IR(KBr) nu 1709 cm-1. Anal. for C15,H12 O2: Calcd. C,80.34; H,5.39. Found C,80.62; H,5.40. |