(6-BROMO-NAPHTHALEN-2-YL)-METHANOL

(6-bromo-2-naphthvπmethanol To a solution of 6-bromo-2-naphthoic acid (1g, 3.98mmol) in THF (20ml) at OInto a 250-mL 3-necked round-bottom flask was placed 6-bromo-2-naphthoic acid (10 g, 39.83 mmol, 1.00 equiv), tetrahydrofuran (40 mL). This was followed by the addition of BH3THF (1 M) (80 mL, 2.00 equiv) dropwise with stirring at 0°C. The resulting solution was stirred overnight at 25°C. The reaction was then quenched by the addition of 100 mL of ice/water. The resulting solution was extracted with 2x200 mL of ethyl acetate and the organic layers were combined. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 8 g (85percent) of (6-bromonaphthalen-2-yl)methanol as a light yellow solid.Preparation of {6- [5- (2-Phenoxy-ethylsulfanylmethyl)- [1, 3, 4] oxadiazol-2-yl] -naphthalen- 2-yl}-methanol a) (6-Bromo-naphthalen-2-yl)-methanol A THF solution of 6-bromo-2-naphthoic acid (3.5 g, 13.94 mmol, 1 eq. ) was cooled to 0°C in an ice bath and then treated dropwise with borane-THF complex (1 M solution in THF, 16.7 mL, 16.7 mmol, 1.2 eq. ) via syringe. After addition was complete, the reaction was allowed to gradually warm to room temperature and stir at that temperature overnight. Several milliliters of water were added to the reaction to quench the remainder of the borane. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was separated and then washed with aqueous 1 M NaOH and then brine. The organic layer was then collected, dried over MgSO4, filtered and the solvent removed in vacuo leaving (6-bromo-naphthalen-2-yl) -methanol (2.56 g, 77percent yield) as a white solid in the flask.To a solution of 6-bromo-2-naphthoic acid (1.0 g, 4.0 mmol) in TUF (20 mL) at 0°C was addedDIBAL-H (8.0 mE, 8.0 mmol). After addition, the reaction mixture was stirred at 25 °C for 16h. The rcaction was quenched by the addition of saturated aqueous NH4C1 (20 mE) arid thenextracted with ethyl acetate (3 x 30 mE). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography(petroleum ether: ethyl acetate 2:1) to give the title compound (0.7 g, 74 percent yield) as a white solid.To a stirred 1.0 M solution of lithium aluminum hydride (108 ML, 108 mmol) was added dropwise over 20 min a solution of methyl 6-bromo-2-naphthoate (18.9 g, 71.3 mmol) in THF (180 ML), while maintaining the reaction temperature below -5° C. Methyl 6-bromo-2-naphthoate (5g, 18.9mmol) was dissolved in purified THF (10OmL) under a nitrogen atmosphere, the reaction solution was cooled down to 0First, 200 g of 6-bromo-2-methyl naphthoate and 1500 ml of tetrahydrofuran were mixed in a reacting flask given a cool bath in a nitrogen atmosphere. In the cool bath, 21.5 g of lithium aluminium hydride was slowly added to the reacting flask to compose a mixture. The mixture was heated to 67° C., refluxed and stirred for two hours. Then, the mixture was bathed in cool water, and 100 g of water was added to the reacting flask to generate a white precipitation. The white precipitation was filtered out of the mixture and dried to obtain a white solid. The white solid was further mixed with water, stirred at room temperature, filtered and dried at 100° C. to obtain (6-bromo-2-naphthyl) methanol in a solid form. 169 g of the white solid was obtained (yield: 94.5percent).Methyl 6-bromo-2-naphthoate (12) (1.5 g, 5.66 mmol) was dissolved in anhydrous THF and cooled to -40 °C in CHTo a solution of LAH (22.8g, 0.6 mol) in THF (1000 mL) was added compound LXI-1 (53.2g, 0.2 mol in THF 1000 mL) dropwise at 0°C. The mixture was stirred for 1.5 h at room temperature, the mixture was quenched with water (22.8 mL) and aq. NaOH (10percent in water, 22.8 mL), then MgS0(6-Bromo-naphthalen-2-yl)-methanol (intermediate)Under a nitrogen atmosphere were placed lithium aluminum hydride to the reactor (5.67g, 149.4mmol) and THF with (100 ml), cooled with ice. There, it was obtained in the first step (T-2) (26.4g, 99.6mmol) and THF (100ml) solution then was dropped in the temperature range of -10 from 0 , and while returning to room temperature It was further stirred for 2 hours. The reaction mixture was ice-cooled, after which ethyl acetate (50ml) was added dropwise thereto in the temperature range of -10 from 0 ° C., 2N-poured into hydrochloric acid (300 ml), stirred for 15 minutes. After the layers were separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were washed with water, saturated aqueous sodium bicarbonate solution, washed sequentially with water, and saturated brine, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to give compound (T-3) (23.6g, 99.6mmol). Compound (T-3) was used in the next reaction without purification.Following related reports,

Molecular Weight:237.09
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:235.98368
Monoisotopic Mass:235.98368
Topological Polar Surface Area:20.2
Heavy Atom Count:13
Complexity:172
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes