1,3-dibromo-2-chlorobenzene

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

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:

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

Procedure: To a solution of 1,3-dibromo-2-chlorobenzene (3.4 g, 12.6 mmol) in dry diethyl ether (60 ml), under nitrogen, at −78° C., was added dropwise n-butyllithium (2.5 M in hexane, 5.0 ml, 12.6 mmol). The mixture was stirred for 1 h after which dimethyldisulfide (1.0 ml, 13.9 mmol) was added dropwise. The resulting mixture was stirred at −78° C. for 30 min and then brought to ambient temperature. Water (100 ml) was added and the mixture was extracted with ethylacetate (3×100 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness. The residue was purified by flash column chromatography (isooctane) to give the title compound (1.23 g). MS m/z (rel. intensity, 70 eV) 240 (M+, 28), 238 (M+, bp), 236 (71), 205 (29), 142 (27). was added dropwise brought to ambient temperature the mixture was extracted with ethylacetate (3×100 ml) The combined organic phases was dried (MgSO4) filtered evaporated to dryness The residue was purified by flash column chromatography (isooctane)

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

Procedure: To a solution of 1,3-dibromo-2-chlorobenzene (3.4 g, 12.6 mmol) in dry diethyl ether (60 ml), under nitrogen, at −78° C., was added dropwise n-butyllithium (2.5 M in hexane, 5.0 ml, 12.6 mmol). The mixture was stirred for 1 h after which dimethyldisulfide (1.0 ml, 13.9 mmol) was added dropwise. The resulting mixture was stirred at −78° C. for 30 min and then brought to ambient temperature. Water (100 ml) was added and the mixture was extracted with ethylacetate (3×100 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness. The residue was purified by flash column chromatography (isooctane) to give the title compound (1.23 g). MS m/z (rel. intensity, 70 eV) 240 (M+, 28), 238 (M+, bp), 236 (71), 205 (29), 142 (27). was added dropwise brought to ambient temperature the mixture was extracted with ethylacetate (3×100 ml) The combined organic phases was dried (MgSO4) filtered evaporated to dryness The residue was purified by flash column chromatography (isooctane)

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

Procedure: To a solution of 1,3-dibromo-2-chlorobenzene (3.4 g, 12.6 mmol) in dry diethyl ether (60 ml), under nitrogen, at −78° C., was added dropwise n-butyllithium (2.5 M in hexane, 5.0 ml, 12.6 mmol). The mixture was stirred for 1 h after which dimethyldisulfide (1.0 ml, 13.9 mmol) was added dropwise. The resulting mixture was stirred at −78° C. for 30 min and then brought to ambient temperature. Water (100 ml) was added and the mixture was extracted with ethylacetate (3×100 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness. was added dropwise brought to ambient temperature the mixture was extracted with ethylacetate (3×100 ml) The combined organic phases was dried (MgSO4) filtered evaporated to dryness

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)