반응 #164532

반응 방정식

4-Fluorobenzoyl chloride

CH2Cl2

paraformaldehyde

→

chloromethyl 4-fluorobenzoate

반응 조건

후처리

1. 1
   기타the solvent was removed under vacuum
2. 2
   workup.ADDITIONWater (50 mL) was added slowly
3. 3
   workup.STIRRINGthe mixture was agitated for 10 min
4. 4
   추출The aqueous layer was extracted with EtOAc (3×50 mL)
5. 5
   세척The combined organic phase was washed with 1 N sodium bicarbonate (2×50 mL)
6. 6
   기타The solvent was removed
7. 7
   기타the product was purified by silica gel chromatography (5% EtOAc-Hexanes)

실험 절차

(Mudryk, B. et al., Tetrahedron Lett. 2002, 43, 6317-6318) 4-Fluorobenzoyl chloride (3.0 g, 18.9 mmol) was added to a stirred suspension of zirconium tetrachloride (4.0 g, 17.01 mmol) in dry CH2Cl2 (40 mL) at room temperature. After 15 min, the reaction mixture was cooled to 0° C. and paraformaldehyde (0.68 g, 22.7 mmol) was added. The slurry was stirred at 0-25° C. for 2 h and the solvent was removed under vacuum. Water (50 mL) was added slowly and the mixture was agitated for 10 min. The aqueous layer was extracted with EtOAc (3×50 mL). The combined organic phase was washed with 1 N sodium bicarbonate (2×50 mL) followed by brine (1×30 mL). The solvent was removed and the product was purified by silica gel chromatography (5% EtOAc-Hexanes). Yield 3.2 g (89%). 1H NMR (500 MHz, CDCl3): δ 5.86 (s, 2H), 7.06 (m, 2H), 8.02 (m, 2H).

출처