1-(5-bromofuran-2-yl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(5-(4-(Trifluoromethyl)phenyl)fur-2-yl)ethanone is prepared from 4-trifluoromethylbenzeneboronic acid and 5-bromo-2-acetylfuran according to general procedure A.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Acetylfuran is dissolved in N,N-dimethylformamide (5 g, 1.1 mol/L), and N-bromosuccinimide (1 eq.) is added.

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of compound 43 (4.8 g, 25.4 mmol) in THF (60 mL) at −78° C., LiHMDS (38 mL, 38.1 mmol) was added dropwise and the reaction stirred −78° C. for 1 h. Ethyl 2,2,2-trifluoroacetate (4.5 g, 38.1 mmol) was then added dropwise. The reaction mixture was allowed to gradually warm to room temperature in cooling bath and stirred overnight. Solvent was removed, cold water (50 mL) was added, and the reaction mixture extracted with diethyl ether (100 mL×3). Combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Crude compound was washed with diethyl ether and hexane to afford compound 44 (5 g, 69%) as a white solid. to gradually warm to room temperature in cooling bath stirred overnight Solvent was removed cold water (50 mL) was added the reaction mixture extracted with diethyl ether (100 mL×3) Combined organic layer was washed with brine dried over sodium sulphate concentrated under reduced pressure Crude compound was washed with diethyl ether and hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(5-(4-(Trifluoromethyl)phenyl)fur-2-yl)ethanone is prepared from 4-trifluoromethylbenzeneboronic acid and 5-bromo-2-acetylfuran according to general procedure A.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(5-(4-(Trifluoromethyl)phenyl)fur-2-yl)ethanone is prepared from 4-trifluoromethylbenzeneboronic acid and 5-bromo-2-acetylfuran according to general procedure A.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Acetylfuran is dissolved in N,N-dimethylformamide (5 g, 1.1 mol/L), and N-bromosuccinimide (1 eq.) is added.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-acetylfuran (20 mmol) in DMF (20 mL) was added portionwise N-bromosuccinimide (22 mmol) with stirring. The reaction mixture was stirred overnight, then poured onto cold water. The product was extracted with ether (200 mL, 3× times). Yield 61%, mp 92-93° C. (hexanes/ether, Lit. mp 94-95° C.; see Gilman H., et al., J. Am. Chem. Soc., 53, 4192-4196 (1931). 1H NMR (CDCl3); δ 2.45 (s, 3H), 6.49 (d, J=3.9 Hz, 1H), 7.12 (d, J=3.6 Hz, 1H). 13C NMR; δ 8185.4, 154.4, 128.2, 118.9,114.3, 25.7. The reaction mixture was stirred overnight The product was extracted with ether (200 mL, 3× times)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a one-neck-flask charged with 2-acetylfuran (5.51 g, 50 mmol) in DMF (40 ml) at 0° C., was added N-Bromosuccinimide (9.79 g, 55.0 mmol) portionwise with stirring. The reaction mixture was stirred at rt overnight. The reaction mixture was poured into water (400 mL), extracted with ether (150 mL×3). The combined organic layers was dried, concentrated and purified on a silica gel column (Hexanes:EtOAc=4:1) to afford a white solid GC-4-89 (3 g, 31.7%). 1H-NMR (400 MHz, CDCl3) δ: 7.12 (d, J=3.6 Hz, 1H), 6.49 (d, J=3.2 Hz, 1H), 2.46 (s, 3H) The reaction mixture was stirred at rt overnight extracted with ether (150 mL×3) The combined organic layers was dried concentrated purified on a silica gel column (Hexanes:EtOAc=4:1) to afford a white solid GC-4-89 (3 g, 31.7%)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of compound 43 (4.8 g, 25.4 mmol) in THF (60 mL) at −78° C., LiHMDS (38 mL, 38.1 mmol) was added dropwise and the reaction stirred −78° C. for 1 h. Ethyl 2,2,2-trifluoroacetate (4.5 g, 38.1 mmol) was then added dropwise. The reaction mixture was allowed to gradually warm to room temperature in cooling bath and stirred overnight. Solvent was removed, cold water (50 mL) was added, and the reaction mixture extracted with diethyl ether (100 mL×3). Combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Crude compound was washed with diethyl ether and hexane to afford compound 44 (5 g, 69%) as a white solid. to gradually warm to room temperature in cooling bath stirred overnight Solvent was removed cold water (50 mL) was added the reaction mixture extracted with diethyl ether (100 mL×3) Combined organic layer was washed with brine dried over sodium sulphate concentrated under reduced pressure Crude compound was washed with diethyl ether and hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(5-(4-(Trifluoromethyl)phenyl)fur-2-yl)ethanone is prepared from 4-trifluoromethylbenzeneboronic acid and 5-bromo-2-acetylfuran according to general procedure A.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Acetylfuran is dissolved in N,N-dimethylformamide (5 g, 1.1 mol/L), and N-bromosuccinimide (1 eq.) is added.