Reaction #324431

Reaction equation

CH2Cl2

NaHCO3

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

N-bromosuccinimide

→

title compound

Yield 38.0%

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

Yield 38.0%

Solvents

CCl4

Conditions

Workup

1. 1
   TemperatureAfter refluxing for 2 h
2. 2
   OtherThe organic portion was separated
3. 3
   Otherdried
4. 4
   Otherto provide the crude residue as a yellow oil
5. 5
   OtherThis material was purified by RP HPLC

Procedure

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