1-bromo-2,3,4,5-tetrafluorobenzene

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

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

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a microwave tube was added 1-bromo-2,3,4,5-tetrafluorobenzene (1.0 g) and 28% aqueous ammonium hydroxide (5 mL). The mixture was heated under microwave irradiation at 150° C. for 2 hrs, then the mixture was poured into water and extracted with hexane. The organic layer was separated, dried with MgSO4, then concentrated. The residue was purified by silica gel flash chromatography (9:1 hexanes/ethyl acetate eluant) afford the title compound as a colorless liquid. 1H NMR (400 MHz, CDCl3) δ 6.75 (m, 1H), 3.95 (br s, 2H) ppm; MS m/z: 226, 228 (M+H)+. extracted with hexane The organic layer was separated dried with MgSO4 concentrated The residue was purified by silica gel flash chromatography (9:1 hexanes/ethyl acetate eluant)

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

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a microwave tube was added 1-bromo-2,3,4,5-tetrafluorobenzene (1.0 g) and 28% aqueous ammonium hydroxide (5 mL). The mixture was heated under microwave irradiation at 150° C. for 2 hrs, then the mixture was poured into water and extracted with hexane. The organic layer was separated, dried with MgSO4, then concentrated. The residue was purified by silica gel flash chromatography (9:1 hexanes/ethyl acetate eluant) afford the title compound as a colorless liquid. 1H NMR (400 MHz, CDCl3) δ 6.75 (m, 1H), 3.95 (br s, 2H) ppm; MS m/z: 226, 228 (M+H)+. extracted with hexane The organic layer was separated dried with MgSO4 concentrated The residue was purified by silica gel flash chromatography (9:1 hexanes/ethyl acetate eluant)

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

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

Procedure: A residue of 3.9 g consisting of bromine and dibromotetrafluorobenzene remains in the boiler in a ratio of about 1:1. The calculated yield to bromotetrafluorobenzene with respect to the distillate is 33.4%.

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

Procedure: A residue of 3.9 g consisting of bromine and dibromotetrafluorobenzene remains in the boiler in a ratio of about 1:1. The calculated yield to bromotetrafluorobenzene with respect to the distillate is 33.4%.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-naphthalen-2-yl ester (259 mg, 0.49 mmol), bis(pinacolato)diboron (151 mg, 0.59 mmol), bis(tricyclohexylphosphine)palladium (0) (75 mg, 0.11 mmol) and cesium fluoride (764 mg, 5.03 mmol) in 20 mL degassed acetonitrile and heat at 100° C. under nitrogen in a sealed vial. The reaction is complete in 10 minutes. Cool and add 1-bromo-2,3,4,5-tetrafluorobenzene (224 mg, 0.99 mmol) along with 10 mL acetonitrile, seal the vial, purge with nitrogen and heat at 80° C. for 2 hours. Cool, filter and purify on an SCX column eluting with 2N ammonia/methanol. Evaporate the solvent and purify the resulting oil on a silica column eluting with 3% methanol/methylene chloride to give 188 mg of the title compound (73%). degassed acetonitrile Cool seal the vial, purge with nitrogen heat at 80° C. for 2 hours Cool filter purify on an SCX column eluting with 2N ammonia/methanol Evaporate the solvent purify the resulting oil on a silica column eluting with 3% methanol/methylene chloride

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a microwave tube was added 1-bromo-2,3,4,5-tetrafluorobenzene (1.0 g) and 28% aqueous ammonium hydroxide (5 mL). The mixture was heated under microwave irradiation at 150° C. for 2 hrs, then the mixture was poured into water and extracted with hexane. The organic layer was separated, dried with MgSO4, then concentrated. The residue was purified by silica gel flash chromatography (9:1 hexanes/ethyl acetate eluant) afford the title compound as a colorless liquid. 1H NMR (400 MHz, CDCl3) δ 6.75 (m, 1H), 3.95 (br s, 2H) ppm; MS m/z: 226, 228 (M+H)+. extracted with hexane The organic layer was separated dried with MgSO4 concentrated The residue was purified by silica gel flash chromatography (9:1 hexanes/ethyl acetate eluant)