Hydrochloric Acid → HCID 10444194, compound

Participants

Reaction Steps

In a similar device as in Example 1 were charged 3.40 g (62.9 mmol) of sodium methoxide and 30 ml of dimethyl sulfoxide under argon atmosphere, then, while stirring at room temperature, 6.30 g (62.9 mmol) of methyl cyanoacetate with a purity of 99% was gradually added dropwise over 5 minutes. Moreover, 10 ml of cyclohexane was added to the mixture, and the temperature of the mixture was raised to 100 to 105° C., formed methanol was subjected to distillation (azeotropic distillation) with cyclohexane. This operation (distillation of methanol) was repeated twice, then, the mixture was cooled to room temperature, 5.10 g (41.9 mmol) of 2,4-difluoronitrobenzene with a purity of 98% was gradually added dropwise to the mixture over 10 minutes while maintaining the temperature to 30 to 40° C., and the resulting mixture was reacted by raising the temperature to 75° C. for one hour. After completion of the reaction, the mixture was cooled to room temperature, then, 100 ml of ethyl acetate was added to the mixture, and 5.25 ml (31.4 mmol) of 6 mol/l hydrochloric acid was gradually added dropwise to the mixture while stirring. Then, the organic layer was separated, and washed successively with 50 ml of water and 50 ml of a saturated saline solution in this order, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography (filler: Daisogel 1002W, eluent:hexane:ethyl acetate=9:1 (volume ratio)) to obtain 5.48 g of methyl 2-(5-fluoro-2-nitrophenyl)-2-cyanoacetate (isolation yield: 71%) as a yellowish oily product with a purity of 97% (areal percentage by high performance liquid chromatography).

Provenance & Evidence