1,2-ETHANEDIOL-(P-BROMOPHENYL)-

General procedure: A glass liner containing a stir bar was charged with substrate (0.5 mmol), base (0.05mmol), Ru-MACHO (5 umol) and MeOH (0.5 mL) in a glove box. The glass linerwas then placed into an autoclave followed by degassing with H2 three times. Thehydrogenation was carried out at 10-50 bar H2 with stirring at 25oC or 80oC for 12-24h. After the reaction finished, the autoclave was allowed to cool down to r.t. Thehydrogen gas was then carefully released in a fume hood, and the solution transferredto a flask with H2O (2 ml), extracted with EA (3x5 ml), dried with Na2SO4 andconcentrated in vacuo to afford the pure product 2a-2s or 3a-3s.4-Bromostyrene (1.0Og, 5.46 mmol) was dissolved in 25 mis of 2: 1 water acetone. To this was added 4-methylmorpholine N-oxide (0.704 g, 6.01 mmole) and osmium tetroxide (0.167 g, 0.061 mmole, 2.5percent in t-BuOH). This mixture was stirred at room temperature for 16 hours, then diluted with EtOAc, washed once with IN aq. HCl, once with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by Flash 40 Biotage ( 4OM cartridge, 100percent EtOAc as the eluant) to give 335 mgs (28percent) of l-(4-bromophenyl)ethane-l, 2-diol as a white solid.[0160] To a solution of ethyl2-(4-bromophenyl)-2-oxoacetate(LOg, 4.0 mmol) in ethanol (20 mL) was added sodiumborohydride (380 mg, 10.0 mmol) at oo C., and the mixturewas stirred at RT for 12 h. The reaction was quenched withpropan-2-one (1 0 mL) and concentrated under reduced pressure.The resultant was purified by silica gel column chromatography( dichloromethane:methanol= 10: 1) to afford thetitle compound (700 mg, 81percent) as a white solid. MS (ES+)C8H9Br02 requires: 216. found: 217, 219 [M+Ht.To a 50 mL round-bottom flask were added ethyl 4-bromobenzoylformate (0.30 g, 1.2 mmol) and methanol (10 mL), then sodium borohydride (0.13 g, 0.41 mmol) was added in portions at 0°C. General procedure: All racemic 1-phenyl-1, 2-ethanediols were prepared in quantitative yields by the reduction of the corresponding substituted phenylglyoxal (1 mmol) with NaBH4 (2 mmol) in ethanol (7 mL) at 0 °C to room temperature for 1 h. After completion of the reaction the excess ethanol was removed. The reaction mixture was hydrolysed with dilute HCl and the mixture was extracted with ethyl acetate. The organic layer was dried, concentrated and purified by column chromatography.To a stirring solution of l-(4-bromophenyl)ethane-l, 2-diol (3.0 g, 14 mmol), in acetonitrile (25 mL), was added concentrated sulfuric acid (7.4 mL, 0.14 mol). The resulting solution was stirred at room temperature for 1 h, then heated to reflux. After 2 h, the mixture was cooled to room temperature and water (10 mL) was added. The acetonitrile was removed by rotary evaporation. The resulting aqueous slurry was heated to 100 0C. After 2 h, the mixture was cooled to room temperature and DCM was added. The mixture was stirred for 5 min before separating the layers. The organic layer was extracted once more with water, then the combined organic extract was set aside. The aqueous extract was treated with 50% aqueous NaOH to pH 10, then extracted with EtOAc (thrice). The combined EtOAc extracts were washed with brine, dried over sodium sulfate, and then the solvents were evaporated to give the title compound (1.9 g, 64%). Exact mass calculated for CsH10BrNO: 215.0, found: LCMS m/z = 216.3 [M+H]+.

Molecular Weight:217.06
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:215.97859
Monoisotopic Mass:215.97859
Topological Polar Surface Area:40.5
Heavy Atom Count:11
Complexity:111
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes