4,4,5,5-tetramethyl-2-(2-methylnaphthalen-1-yl)-1,3,2-dioxaborolane

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

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

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

Procedure: The title compound, MS: m/e=315.3 (M+H+), was prepared from 4,4,5,5-tetramethyl-2-(2-methyl-naphthalen-1-yl)-[1,3,2]dioxaborolane and 5-chloro-3-(2-methyl-imidazol-1-yl-methyl)-pyridazine.

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

Procedure: The title compound, MS: m/e=315.3 (M+H+), was prepared from 4,4,5,5-tetramethyl-2-(2-methyl-naphthalen-1-yl)-[1,3,2]dioxaborolane and 5-chloro-3-(2-methyl-imidazol-1-yl-methyl)-pyridazine.

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 47.3 g (176 mmol) of 4,4,5,5-tetramethyl-2-(2-methyl-1-naphthyl)-1,3,2-dioxaborolane, 33.0 g (185 mmol) of NBS and 0.17 g of benzoyl peroxide in 340 ml of CCl4 was stirred at 75° C. for 14 h. Further on, the reaction mixture was cooled to room temperature, filtered through glass frit (G3), and the filtrate was evaporated to dryness. This procedure gave 62.2 g (99%) of beige solid. Anal. calc. for C17H20BBrO2: C, 58.83; H, 5.81. Found: C, 59.00; H, 5.95. 1H NMR (CDCl3): δ 8.30 (m, 1H, 8-H), 7.84 (d, J=8.3 Hz, 1H, 4-H), 7.79 (m, 1H, 5-H), 7.43-7.52 (m, 3H, 3, 6, 7-H), 4.96 (s, 2H, CH2Br), 1.51 (s, 12H, CMe2CMe2). Further on, the reaction mixture was cooled to room temperature filtered through glass frit (G3) the filtrate was evaporated to dryness

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

Procedure: 1.2-Dibromoethane (˜0.3 ml) was added to 6.10 g (250 mmol) magnesium turnings in 1000 cm3 of THF. This mixture was stirred for 10 min, and then 55.3 g (250 mmol) of 1-bromo-2-methylnaphtalene was added for 1 h by vigorous stirring at room temperature for 3.5 h. Further on, 46.5 g (250 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added in one portion. The resulting mixture was stirred for 15 min and then was poured into 1000 cm3 of cold water. The product was extracted with 3×300 ml of ethyl acetate. The organic layer was separated, washed by water, brine, then dried over MgSO4, and, finally, evaporated to dryness. The resulting white solid was washed by 2×75 ml of pentane and dried in a vacuum. Yield 47.3 g (70%). Anal. calc. for C17H21BO2: C, 76.14; H, 7.89. Found: C, 76.31; H, 8.02. 1H NMR (CDCl3): δ 8.12 (m, 1H, 8-H), 7.77 (m, 1H, 5-H), 7.75 (d, J=8.4 Hz, 1H, 4-H), 7.44 (m, 1H, 7-H), 7.38 (m, 1H, 6-H), 7.28 (d, J=8.4 Hz, 1H, 3-H), 2.63 (s, 3H, 2-Me), 1.48 (s, 12H, CMe2CMe2). by vigorous stirring at room temperature for 3.5 h The resulting mixture was stirred for 15 min The product was extracted with 3×300 ml of ethyl acetate The organic layer was separated washed by water, brine dried over MgSO4 finally, evaporated to dryness The resulting white solid was washed by 2×75 ml of pentane dried in a vacuum

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 47.3 g (176 mmol) of 4,4,5,5-tetramethyl-2-(2-methyl-1-naphthyl)-1,3,2-dioxaborolane, 33.0 g (185 mmol) of NBS, and 0.17 g (0.70 mmol) of benzoyl peroxide in 340 ml of CCl4 was stirred in argon atmosphere for 14 h at 75° C. The resulting mixture was cooled to room temperature, filtered through a glass frit (G3), and the filtrate was evaporated to dryness. This procedure gave 62.2 g (99%) of a beige solid. Anal. calc. for C17H20BBrO2: C, 58.83; H, 5.81. Found: C, 58.75; H, 5.90. 1H NMR (CDCl3): δ 8.30 (m, 1H, 8-H), 7.84 (d, J=8.3 Hz, 1H, 4-H), 7.79 (m, 1H, 5-H), 7.43-7.52 (m, 3H, 3,6,7-H), 4.96 (s, 2H, CH2Br), 1.51 (s, 12H, CMe2CMe2). The resulting mixture was cooled to room temperature filtered through a glass frit (G3) the filtrate was evaporated to dryness

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

Procedure: 1,2-Dibromoethane (˜0.3 ml) was added to 6.10 g (0.25 mol) of magnesium turnings in 1000 cm3 of THF. This mixture was stirred for 10 min, and then 55.3 g (0.25 mol) of 1-bromo-2-methylnaphtalene was added by vigorous stirring for 3.5 h at room temperature. Further on, 46.5 g (250 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added in one portion. The resulting mixture was stirred for 15 min and then poured into 1000 cm3 of cold water. The product was extracted with 3×300 ml of ethyl acetate. The organic layer was separated, washed by water, brine, dried over MgSO4, and, finally, evaporated to dryness. The formed white solid was washed by 2×75 ml of pentane and then dried in vacuum. Yield 47.3 g (70%). Anal. calc. for C17H21BO2: C, 76.14; H, 7.89. Found: C, 76.21; H, 7.96. 1H NMR (CDCl3): δ 8.12 (m, 1H, 8-H), 7.77 (m, 1H, 5-H), 7.75 (d, J=8.4 Hz, 1H, 4-H), 7.44 (m, 1H, 7-H), 7.38 (m, 1H, 6-H), 7.28 (d, J=8.4 Hz, 1H, 3-H), 2.63 (s, 3H, 2-Me), 1.48 (s, 12H, CMe2CMe2). by vigorous stirring for 3.5 h at room temperature The resulting mixture was stirred for 15 min The product was extracted with 3×300 ml of ethyl acetate The organic layer was separated washed by water, brine dried over MgSO4 finally, evaporated to dryness The formed white solid was washed by 2×75 ml of pentane dried in vacuum

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

Procedure: 1,2-Dibromoethane (˜0.3 ml) was added to 6.10 g (0.25 mol) of magnesium turnings in 1000 cm3 of THF. This mixture was stirred for 10 min, and then 55.3 g (0.25 mol) of 1-bromo-2-methylnaphtalene was added by vigorous stirring for 3.5 h at room temperature. Further on, 46.5 g (250 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added in one portion. The resulting mixture was stirred for 15 min and then poured into 1000 cm3 of cold water. The product was extracted with 3×300 ml of ethyl acetate. The organic layer was separated, washed by water, brine, dried over MgSO4, and, finally, evaporated to dryness. The formed white solid was washed by 2×75 ml of pentane and then dried in vacuum. Yield 47.3 g (70%). Anal. calc. for C17H21BO2: C, 76.14; H, 7.89. Found: C, 76.21; H, 7.96. 1H NMR (CDCl3): δ 8.12 (m, 1H, 8-H), 7.77 (m, 1H, 5-H), 7.75 (d, J=8.4 Hz, 1H, 4-H), 7.44 (m, 1H, 7-H), 7.38 (m, 1H, 6-H), 7.28 (d, J=8.4 Hz, 1H, 3-H), 2.63 (s, 3H, 2-Me), 1.48 (s, 12H, CMe2CMe2). by vigorous stirring for 3.5 h at room temperature The resulting mixture was stirred for 15 min The product was extracted with 3×300 ml of ethyl acetate The organic layer was separated washed by water, brine dried over MgSO4 finally, evaporated to dryness The formed white solid was washed by 2×75 ml of pentane dried in vacuum

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 47.3 g (176 mmol) of 4,4,5,5-tetramethyl-2-(2-methyl-1-naphthyl)-1,3,2-dioxaborolane, 33.0 g (185 mmol) of NBS (N-Bromosuccinimide) and 0.17 g of benzoyl peroxide in 340 ml of CCl4 was stirred at 75° C. for 14 h. Thereafter the reaction mixture was cooled to room temperature, filtered through glass frit (G3), and the filtrate was evaporated to dryness. This procedure gave 62.2 g (99%) of beige solid. Anal. calc. for C17H20BBrO2: C, 58.83; H, 5.81. Found: C, 59.00; H, 5.95. 1H NMR (CDCl3): 8.30 (m, 1H, 8-H), 7.84 (d, J=8.3 Hz, 1H, 4-H), 7.79 (m, 1H, 5-H), 7.43-7.52 (m, 3H, 3,6,7-H), 4.96 (s, 2H, CH2Br), 1.51 (s, 12H, CMe2CMe2). Thereafter the reaction mixture was cooled to room temperature filtered through glass frit (G3) the filtrate was evaporated to dryness

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 47.3 g (176 mmol) of 4,4,5,5-tetramethyl-2-(2-methyl-1-naphthyl)-1,3,2-dioxaborolane, 33.0 g (185 mmol) of NBS (N-Bromosuccinimide) and 0.17 g of benzoyl peroxide in 340 ml of CCl4 was stirred at 75° C. for 14 h. Thereafter the reaction mixture was cooled to room temperature, filtered through glass frit (G3), and the filtrate was evaporated to dryness. This procedure gave 62.2 g (99%) of beige solid. Anal. calc. for C17H20BBrO2: C, 58.83; H, 5.81. Found: C, 59.00; H, 5.95. 1H NMR (CDCl3): 8.30 (m, 1H, 8-H), 7.84 (d, J=8.3 Hz, 1H, 4-H), 7.79 (m, 1H, 5-H), 7.43-7.52 (m, 3H, 3,6,7-H), 4.96 (s, 2H, CH2Br), 1.51 (s, 12H, CMe2CMe2). Thereafter the reaction mixture was cooled to room temperature filtered through glass frit (G3) the filtrate was evaporated to dryness

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

Procedure: 1,2-Dibromoethane (˜0.3 ml) was added to 6.10 g (250 mmol) magnesium turnings in 1000 cm3 of THF. This mixture was stirred for 10 min, and then 55.3 g (250 mmol) of 1-bromo-2-methylnaphthalene was added for 1 h by vigorous stirring at room temperature for 3.5 h. Thereafter, 46.5 g (250 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added in one portion. The resulting mixture was stirred for 15 minutes and then was poured into 1000 cm3 of cold water. The product was extracted with 3×300 ml of ethyl acetate. The organic layer was separated, washed by water, brine, then dried over MgSO4, and, finally, evaporated to dryness. The resulting white solid was washed by 2×75 ml of pentane and dried in vacuum. Yield 47.3 g (70%). Anal. calc. for C17H21BO2: C, 76.14; H, 7.89. Found: C, 76.31; H, 8.02. 1H NMR (CDCl3): 8.12 (m, 1H, 8-H), 7.77 (m, 1H, 5-H), 7.75 (d, J=8.4 Hz, 1H, 4-H), 7.44 (m, 1H, 7-H), 7.38 (m, 1H, 6-H), 7.28 (d, J=8.4 Hz, 1H, 3-H), 2.63 (s, 3H, 2-Me), 1.48 (s, 12H, CMe2CMe2). by vigorous stirring at room temperature for 3.5 h The resulting mixture was stirred for 15 minutes The product was extracted with 3×300 ml of ethyl acetate The organic layer was separated washed by water, brine dried over MgSO4 finally, evaporated to dryness The resulting white solid was washed by 2×75 ml of pentane dried in vacuum