Réaction #324431

Équation de réaction

CH2Cl2

NaHCO3

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

N-bromosuccinimide

→

title compound

Rendement 38.0%

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

Rendement 38.0%

Solvants

CCl4

Conditions de réaction

Traitement

1. 1
   TempératureAfter refluxing for 2 h
2. 2
   AutreThe organic portion was separated
3. 3
   Autredried
4. 4
   Autreto provide the crude residue as a yellow oil
5. 5
   AutreThis material was purified by RP HPLC

Mode opératoire

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).

Source