1-(2-bromophenyl)-2-methylpropan-2-ol

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

Procedure: To a solution of 1-(2-bromophenyl)-2-methylpropan-2-ol (3.48 g, 15 mmol) in THF (100 mL) cooled to −78° C. was added n-butyllithium (15.2 mL, 2.5M in hexanes) in a dropwise fashion. The reaction was permitted to stir for 10 minutes, prior to the addition of triisopropylborate (10.5 mL, 45 mmol). The reaction was permitted to stir for 16 hours, gradually warming to room temperature. Aqueous hydrochloric acid (10 mL, 6M) was added, and the mixture stirred for 1 hour. The reaction was diluted with EtOAc (250 mL) and water (50 mL). The organic portion was washed with brine, dried over sodium sulfate, and evaporated. The resultant crude material was purified by silica gel chromatography to yield 3,3-Dimethyl-3,4-dihydro-benzo[c][1,2]oxaborinin-1-ol as a white semisolid product. 1H NMR (400 MHz, acetone) δ ppm 1.13 (s, 6H) 2.76 (s, 2H) 6.99-7.04 (m, 1H) 7.05-7.14 (m, 1H) 7.21-7.27 (m, 1H) 7.58-7.64 (m, 1H). Amount obtained: 830 mg, 31% yield. to stir for 16 hours the mixture stirred for 1 hour The organic portion was washed with brine dried over sodium sulfate evaporated The resultant crude material was purified by silica gel chromatography

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

Procedure: To a solution of 1-(2-bromophenyl)-2-methylpropan-2-ol (3.48 g, 15 mmol) in THF (100 mL) cooled to −78° C. was added n-butyllithium (15.2 mL, 2.5M in hexanes) in a dropwise fashion. The reaction was permitted to stir for 10 minutes, prior to the addition of triisopropylborate (10.5 mL, 45 mmol). The reaction was permitted to stir for 16 hours, gradually warming to room temperature. Aqueous hydrochloric acid (10 mL, 6M) was added, and the mixture stirred for 1 hour. The reaction was diluted with EtOAc (250 mL) and water (50 mL). The organic portion was washed with brine, dried over sodium sulfate, and evaporated. The resultant crude material was purified by silica gel chromatography to yield 3,3-Dimethyl-3,4-dihydro-benzo[c][1,2]oxaborinin-1-ol as a white semisolid product. 1H NMR (400 MHz, acetone) δ ppm 1.13 (s, 6H) 2.76 (s, 2H) 6.99-7.04 (m, 1H) 7.05-7.14 (m, 1H) 7.21-7.27 (m, 1H) 7.58-7.64 (m, 1H). Amount obtained: 830 mg, 31% yield. to stir for 16 hours the mixture stirred for 1 hour The organic portion was washed with brine dried over sodium sulfate evaporated The resultant crude material was purified by silica gel chromatography