1-bromo-2-chloro-3-prop-1-ynylbenzene

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

Procedure: To a microwave vial were added 1,3-dibromo-2-chlorobenzene (780 mg, 2.89 mmol), trimethyl(prop-1-ynyl)silane (0.645 mL, 4.33 mmol), copper iodide (28 mg, 0.14 mmol), PdCl2(dppf) CH2Cl2 (118 mg, 0.14 mmol), tetrabutylammonium fluoride (1 M in THF, 8.66 mL, 8.66 mmol), diisopropylamine (1.23 mL, 8.66 mmol) and anhydrous DMF (5 mL). The vial was capped and purged with argon and the mixture was irradiated at 100° C. for 1 h in a microwave reactor. The mixture was diluted with water and extracted with DCM three times, dried through a phase separator and concentrated in vacuo. The product was purified by flash chromatography (100% heptanes as eluent) to give 146 mg (22% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.13 (s, 3 H) 7.24 (t, J=7.88 Hz, 1 H) 7.53 (dd, J=7.57, 1.26 Hz, 1 H) 7.74 (dd, J=8.04, 1.42 Hz, 1 H); MS (CI) m/z 231 [M+H]+. The vial was capped purged with argon the mixture was irradiated at 100° C. for 1 h in a microwave reactor The mixture was diluted with water extracted with DCM three times dried through a phase separator concentrated in vacuo The product was purified by flash chromatography (100% heptanes as eluent)

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

Procedure: To a microwave vial were added 1,3-dibromo-2-chlorobenzene (780 mg, 2.89 mmol), trimethyl(prop-1-ynyl)silane (0.645 mL, 4.33 mmol), copper iodide (28 mg, 0.14 mmol), PdCl2(dppf) CH2Cl2 (118 mg, 0.14 mmol), tetrabutylammonium fluoride (1 M in THF, 8.66 mL, 8.66 mmol), diisopropylamine (1.23 mL, 8.66 mmol) and anhydrous DMF (5 mL). The vial was capped and purged with argon and the mixture was irradiated at 100° C. for 1 h in a microwave reactor. The mixture was diluted with water and extracted with DCM three times, dried through a phase separator and concentrated in vacuo. The product was purified by flash chromatography (100% heptanes as eluent) to give 146 mg (22% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.13 (s, 3 H) 7.24 (t, J=7.88 Hz, 1 H) 7.53 (dd, J=7.57, 1.26 Hz, 1 H) 7.74 (dd, J=8.04, 1.42 Hz, 1 H); MS (CI) m/z 231 [M+H]+. The vial was capped purged with argon the mixture was irradiated at 100° C. for 1 h in a microwave reactor The mixture was diluted with water extracted with DCM three times dried through a phase separator concentrated in vacuo The product was purified by flash chromatography (100% heptanes as eluent)

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

Procedure: To a microwave vial were added 1,3-dibromo-2-chlorobenzene (780 mg, 2.89 mmol), trimethyl(prop-1-ynyl)silane (0.645 mL, 4.33 mmol), copper iodide (28 mg, 0.14 mmol), PdCl2(dppf) CH2Cl2 (118 mg, 0.14 mmol), tetrabutylammonium fluoride (1 M in THF, 8.66 mL, 8.66 mmol), diisopropylamine (1.23 mL, 8.66 mmol) and anhydrous DMF (5 mL). The vial was capped and purged with argon and the mixture was irradiated at 100° C. for 1 h in a microwave reactor. The mixture was diluted with water and extracted with DCM three times, dried through a phase separator and concentrated in vacuo. The product was purified by flash chromatography (100% heptanes as eluent) to give 146 mg (22% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.13 (s, 3 H) 7.24 (t, J=7.88 Hz, 1 H) 7.53 (dd, J=7.57, 1.26 Hz, 1 H) 7.74 (dd, J=8.04, 1.42 Hz, 1 H); MS (CI) m/z 231 [M+H]1. The vial was capped purged with argon the mixture was irradiated at 100° C. for 1 h in a microwave reactor The mixture was diluted with water extracted with DCM three times dried through a phase separator concentrated in vacuo The product was purified by flash chromatography (100% heptanes as eluent)

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

Procedure: To a microwave vial were added 1,3-dibromo-2-chlorobenzene (780 mg, 2.89 mmol), trimethyl(prop-1-ynyl)silane (0.645 mL, 4.33 mmol), copper iodide (28 mg, 0.14 mmol), PdCl2(dppf) CH2Cl2 (118 mg, 0.14 mmol), tetrabutylammonium fluoride (1 M in THF, 8.66 mL, 8.66 mmol), diisopropylamine (1.23 mL, 8.66 mmol) and anhydrous DMF (5 mL). The vial was capped and purged with argon and the mixture was irradiated at 100° C. for 1 h in a microwave reactor. The mixture was diluted with water and extracted with DCM three times, dried through a phase separator and concentrated in vacuo. The product was purified by flash chromatography (100% heptanes as eluent) to give 146 mg (22% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.13 (s, 3H) 7.24 (t, J=7.88 Hz, 1H) 7.53 (dd, J=7.57, 1.26 Hz, 1H) 7.74 (dd, J=8.04, 1.42 Hz, 1H); MS (CI) m/z 231 [M+H] The vial was capped purged with argon the mixture was irradiated at 100° C. for 1 h in a microwave reactor The mixture was diluted with water extracted with DCM three times dried through a phase separator concentrated in vacuo The product was purified by flash chromatography (100% heptanes as eluent)

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

Procedure: To a microwave vial were added 1,3-dibromo-2-chlorobenzene (780 mg, 2.89 mmol), trimethyl(prop-1-ynyl)silane (0.645 mL, 4.33 mmol), copper iodide (28 mg, 0.14 mmol), PdCl2(dppf) CH2Cl2 (118 mg, 0.14 mmol), tetrabutylammonium fluoride (1 M in THF, 8.66 mL, 8.66 mmol), diisopropylamine (1.23 mL, 8.66 mmol) and anhydrous DMF (5 mL). The vial was capped and purged with argon and the mixture was irradiated at 100° C. for 1 h in a microwave reactor. The mixture was diluted with water and extracted with DCM three times, dried through a phase separator and concentrated in vacuo. The product was purified by flash chromatography (100% heptanes as eluent) to give 146 mg (22% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.13 (s, 3 H) 7.24 (t, J=7.88 Hz, 1 H) 7.53 (dd, J=7.57, 1.26 Hz, 1 H) 7.74 (dd, J=8.04, 1.42 Hz, 1 H); MS (CI) m/z 231 [M+H]+. The vial was capped purged with argon the mixture was irradiated at 100° C. for 1 h in a microwave reactor The mixture was diluted with water extracted with DCM three times dried through a phase separator concentrated in vacuo The product was purified by flash chromatography (100% heptanes as eluent)