반응 #10373

반응 방정식

hydrochloric acid

2,4,5-Trifluoro-3-formylbenzoic acid

triethylamine

O-benzylhydroxylamine hydrochloride

→

3-(benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid

수율 100.0%

용매

tetrahydrofuran

brine

반응 조건

후처리

1. 1
   추출The mixture is extracted with ethyl acetate
2. 2
   건조The organic phase is dried over Na2SO4
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo

실험 절차

2,4,5-Trifluoro-3-formylbenzoic acid (Horiuchi N., Yonezawa T., Chiba K., Yoshida H., PCT Int. Appl. [1999] WO 97-JP2918), (5.70 g, 27.9 mmol), triethylamine (11 mL, 78.9 mmol), O-benzylhydroxylamine hydrochloride (4.47 g, 28.0 mmol) and anhydrous tetrahydrofuran (150 mL) are stirred at room temperature for 50 hours. The mixture is poured into brine and the pH adjusted to 5.5–6.0 using 1.0 M hydrochloric acid. The mixture is extracted with ethyl acetate. The organic phase is dried over Na2SO4, filtered, and concentrated in vacuo to provide 3-(benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid (8.63 g), which is used without further purification. 1H NMR (200 MHz, CDCl3): δ 9.82–9.18 (bs, 1H), 8.24 (s, 1H), 7.94–7.68 (m, 1H), 7.55–7.23 (m, 5H), 5.23 (d, 2H). MS (EI, M−1) m/z 308.

출처