تفاعل #324431

معادلة التفاعل

CH2Cl2

NaHCO3

5-methyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester

N-bromosuccinimide

→

title compound

المردود 38.0%

5-Bromomethyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester

المردود 38.0%

المذيبات

CCl4

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter refluxing for 2 h
2. 2
   أخرىThe organic portion was separated
3. 3
   أخرىdried
4. 4
   أخرىto provide the crude residue as a yellow oil
5. 5
   أخرىThis material was purified by RP HPLC

الإجراء التجريبي

To a solution of 5-methyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester (0.95 g, 4.5 mmol) in CCl4 (12 mL) was added N-bromosuccinimide (0.84 g, 4.8 mmol) followed by AIBN (0.004 g, 0.01 mmol). After refluxing for 2 h, analytical HPLC analysis confirmed the reaction was complete. The reaction was cooled to rt, then CH2Cl2 and sat'd NaHCO3 (aq.) were added. The organic portion was separated and dried to provide the crude residue as a yellow oil. This material was purified by RP HPLC to provide the title compound (510 mg, 38%). MS (ESI): mass calcd. for C9H8BrF3O3, 300.0; m/z found, 302.9 [M+H]+. 1H NMR (CDCl3): 6.84 (s, 1H), 4.44 (s, 2H), 4.34 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.1 Hz, 3H).

المصدر