3,3-diMethylbenzo[c][1,2]oxaborol-1(3H)-ol

To a solution of n-BuLi (166 mL, 2.6 M, 432 mmol) in 200 mL of THF at -78° C. under argon was slowly added a solution of Compound 10d (42.2 g, 196 mmol) in 60 mL of THF at a rate that the internal temperature remained below -70° C. The mixture was stirred at -75° C. for 2 h. To the reaction mixture was then added triisopropylborate (59 mL, 255 mmol) in three portions. The mixture was allowed to warm slowly to room temperature overnight. The mixture was then cooled to 0° C., and was carefully quenched with dilute hydrochloric acid (250 mL, 2N). The mixture was then stirred at room temperature for 1 h. The pH of the mixture was checked and adjusted to acidic using additional 2N HCl if prophetic. The two layers were separated, and the aqueous layer was extracted twice with ether. The organic layers were combined, and dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield a pale yellow oil. The residue was then diluted with ethyl acetate (400 mL) and, washed with 1N sodium hydroxide solution (150 mL.x.3). The basic aqueous layers were combined and acidified with 2N HCl. The clear solution turned cloudy when the acid was added. The mixture was extracted with ether (150 mL.x.3). The organic layers were combined and dried with magnesium sulfate. The solution was filtered, and the filtrate was concentrated under reduced pressure to yield the title Compound 10e as a colorless oil (26.2 g, 82percent) which was used without further purification in the next step. 82c[0384] A 50 mL round-bottomed-flask equipped with a magnetic stir bar and ice- HA 12-Liter 4-neck round bottom flask equipped with a thermocouple, condenser, addition funnel and overhead mechanical stirrer under dry Argon was charged with anhydrous THF, (3 L) and chilled to -70 to -78° C. via a dry ice/acetone bath. n-Butyl lithium (2.5N in hexanes, 860 mL, 2.15 mol) was slowly added via addition funnel. An exotherm was observed as the temperature rose from -78 to -70° C. To the addition funnel was added a solution of Compound 10d (220 g, 979.97 mmol) in anhydrous THF (1 L). The 2-(2-bromophenyl)propan-2-ol solution was slowly added to the n-BuLi solution. The addition took 90 min in order to maintain a reaction temperature below -70° C. After the addition was complete, the reaction mixture was stirred at -70 to -75° C. for 30 min. The triethylborate (230 mL, 1.35 mol) was quickly added in 3 portions at -70° C. An exotherm was observed, the batch temperature rose from -70 to -64° C. The reaction was stirred at -70° C. and slowly warmed to room temperature over night. After the reaction was cooled to 0-5° C., the reaction was slowly quenched with 2 M HCl (1 L, 2.00 mol) added via the addition funnel while maintaining the batch temperature 0-5° C. The reaction mixture was stirred for 1 h. The aqueous phase pH was 9-10. The pH was then adjusted to acidic (4-5) with 2 M HCl (200 mL). The two phases were separated and the aqueous layer was extracted with MTBE (2.x.500 mL). The combined organic phases were dried with anhydrous magnesium sulfate. The solution was filtered and concentrated to yield a yellow oil. The yellow oil was diluted with MTBE (1.5 L) and washed with 1M NaOH (3.x.500 mL). The product containing basic aqueous phases were combined and acidified with 2 M HCl (800 mL) (the clear solution turns turbid with the addition of acid). After stirring the turbid solution for 15 min (pH=4-5) (Note 1), it was extracted with MTBE (2.x.500 mL). The organic phases were combined and dried over MgSOStep 2[00253] To a solution of n-BuLi (21.2ml, 0.053 mol) in anhydrous THF (160 mL) at - 78°C under argon was slowly added a solution of 2-(2-bromophenyl)propan-2-ol (XCV) (0.0212 mol, 4.55 g) in anhydrous THF (50 mL) while maintaining the temperature below -65°C. After addition was complete, the reaction mixture was stirred at -75°C for 30 min. To this mixture was added in portions trimethyl borate (0.032mol, 3.3 g), and the reaction mixture was stirred at - 78°C for 30 min and then at room temperature overnight. The mixture was cooled to 0°C, carefully quenched with 1M aqueous HCl, and stirred at room temperature for 15 min. The mixture was acidified to pH 3 with 2M HCl and stirring was continued for 1 hour. The two phases were separated and the aqueous layer was extracted with EtOAc. The combined organic phases were dried over MgS09 N-(3, 3-Dimethyl-l-phenyl-2, 3-dihvdro-lH-benzotblborol-6-yl)-4-fluoro-2- trifluoromethylbenzatnideHNOC. General procedure: A glass vial equipped with a magnetic stir bar and fitted with a Teflon screw cap was charged with BBA (90 mg, 1.0 mmol), KOAc (98 mg, 1.0 mmol) and the aryl halide (0.50 mmol). To this vessel was added EtOH (2.5 mL) and the reaction media was degassed with Argon for 5 minutes. XPhos Pd G2 (79 mg, 10 molpercent) was then added, and the solution was stirred (750 rpm) and heated at 80°C until full conversion was observed. The reaction media was filtered over celite and the crude filtrate was purified using Teledyne Isco Combiflash device (silica gel column chromatography 15 μm) and Hept:DCM (90:10 to 0:100) as solvent.[0379] To a solution of 2-(2'-bromophenyl)-6-butyl[l, 3, 6, 2]dioxazaborocan (3.0g, 9.2 mmol) in THF (76 mL) at -78

Molecular Weight:162.00
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:162.0852098
Monoisotopic Mass:162.0852098
Topological Polar Surface Area:29.5
Heavy Atom Count:12
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes