(3,4,5-trichlorophenyl)boronic acid

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

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,4,5-trichlorophenylboronic acid (4.5 g, 20 mmol), 2-bromo-3,3,3-trifluoro-prop-1-ene (4.9 g, 28 mmol), Cs2CO3 (20 mL, 2 M, 40 mmol) and Pd(PPh3)2Cl2 (421 mg) in THF (30 mL) was heated at 70° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between ether and H2O. The aqueous layer was extracted with EA and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography over silica gel eluted with hexanes to give 1,2,3-trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (4.3 g; yield 80%). 1H NMR (500 MHz, CDCl3): δ 7.40 (s, 2H), 5.99 (s, 1H), 5.76 (s, 1H) ppm. The mixture was cooled to rt partitioned between ether and H2O The aqueous layer was extracted with EA the combined organic layers were dried over Na2SO4 The solvent was removed under reduced pressure the crude product was purified by column chromatography over silica gel eluted with hexanes

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,4,5-trichlorophenylboronic acid (3.376 g, 15 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (4.02 g, 23 mmol), K2CO3 (4.15 g, 30 mmol) and Pd(PPh3)2Cl2 (4.15 g, 30 mmol) in THF (16 mL) and H2O (8 mL) was heated at 80° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between EA (50 mL) and H2O (50 mL). The aqueous layer was extracted with EA (50 mL) and the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel to give the crude desired product (3.7 g; 90% yield) as a pale yellow solid. The mixture was cooled to rt partitioned between EA (50 mL) and H2O (50 mL) The aqueous layer was extracted with EA (50 mL) the combined organic layers were dried over anhydrous Na2SO4 The solvent was removed under reduced pressure the crude product was purified by column chromatography on silica gel

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,4,5-trichlorophenylboronic acid (3.376 g, 15 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (4.02 g, 23 mmol), K2CO3 (4.15 g, 30 mmol) and Pd(PPh3)2Cl2 (4.15 g, 30 mmol) in THF (16 mL) and H2O (8 mL) was heated at 80° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between EA (50 mL) and H2O (50 mL). The aqueous layer was extracted with EA (50 mL) and the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel to give the crude desired product (3.7 g; 90% yield) as a pale yellow solid. The mixture was cooled to rt partitioned between EA (50 mL) and H2O (50 mL) The aqueous layer was extracted with EA (50 mL) the combined organic layers were dried over anhydrous Na2SO4 The solvent was removed under reduced pressure the crude product was purified by column chromatography on silica gel

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,4,5-trichlorophenylboronic acid (4.5 g, 20 mmol), 2-bromo-3,3,3-trifluoro-prop-1-ene (4.9 g, 28 mmol), Cs2CO3 (20 mL, 2 M, 40 mmol) and Pd(PPh3)2Cl2 (421 mg) in THF (30 mL) was heated at 70° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between ether and H2O. The aqueous layer was extracted with EA and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography over silica gel eluted with hexanes to give 1,2,3-trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (4.3 g; yield 80%). 1H NMR (500 MHz, CDCl3): δ 7.40 (s, 2H), 5.99 (s, 1H), 5.76 (s, 1H) ppm. The mixture was cooled to rt partitioned between ether and H2O The aqueous layer was extracted with EA the combined organic layers were dried over Na2SO4 The solvent was removed under reduced pressure the crude product was purified by column chromatography over silica gel eluted with hexanes

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,4,5-trichlorophenylboronic acid (3.376 g, 15 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (4.02 g, 23 mmol), K2CO3 (4.15 g, 30 mmol) and Pd(PPh3)2Cl2 (4.15 g, 30 mmol) in THF (16 mL) and H2O (8 mL) was heated at 80° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between EA (50 mL) and H2O (50 mL). The aqueous layer was extracted with EA (50 mL) and the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel to give the crude desired product (3.7 g; 90% yield) as a pale yellow solid. The mixture was cooled to rt partitioned between EA (50 mL) and H2O (50 mL) The aqueous layer was extracted with EA (50 mL) the combined organic layers were dried over anhydrous Na2SO4 The solvent was removed under reduced pressure the crude product was purified by column chromatography on silica gel