تفاعل #10373

معادلة التفاعل

hydrochloric acid

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

triethylamine

O-benzylhydroxylamine hydrochloride

→

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

المردود 100.0%

المذيبات

tetrahydrofuran

brine

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe mixture is extracted with ethyl acetate
2. 2
   تجفيفThe organic phase is dried over Na2SO4
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo

الإجراء التجريبي

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.

المصدر