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To a refluxing mixture of potassium tert-butoxide (27 g, 242 mmol) and tert-butanol (150 mL) was added a solution of 4-fluoro-benzaldehyde (20 g, 161 mmol) and dimethyl succinate (28 g, 193.2 mmol) in tert-butanol (100 mL) dropwise. After being heated at reflux for 3 hours, the mixture was concentrated in vacuo to remove tert-butanol. The residue was dissolved in 1 N hydrochloric acid (180 mL). The resulting aqueous solution was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (elution with 30% ethyl acetate in petroleum ether) to afford 2-(4-fluoro-benzylidene)-succinic acid 1-methyl ester (25.5 g, 66%) as a light yellow solid. 1H NMR (400 MHz, CD3OD) δ ppm 7.84 (s, 1H), 7.41-7.46 (m, 2H), 7.13-7.20 (m, 2H), 3.81 (s, 3H), 3.49 (s, 2H).

1. temperatureAfter being heated
2. temperatureat reflux for 3 hours
3. concentrationthe mixture was concentrated in vacuo
4. customto remove tert-butanol
5. dissolutionThe residue was dissolved in 1 N hydrochloric acid (180 mL)
6. extractionThe resulting aqueous solution was extracted with ethyl acetate (100 mL×3)
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customThe residue was purified by column chromatography (elution with 30% ethyl acetate in petroleum ether)