6-BROMO-2,3-DIHYDRO-1H-INDEN-1-OL

168.8g compd. 6 and 650 ml of ethanol is added during the reaction of the bottle. Next, the water temperature is lower than 10 °C, NaBHExample 10 Part A, To a solution of 6-bromo-2, 3-dihydro-1 H-inden-1 -one (5 g, 23.69 mmol) in methanol (50 mL) was added sodium borohydride (0.896 g, 23.69 mmol) under N2 protection. The reaction mixture was stirred for 2 h at ambient temperature. Then the solvent was removed by reduced pressure. The residue was dissolved inlOO mL of ethyl acetate and 20 mL of 1 N HCI. The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 30 mL). Thecombined organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated to afford the title compound 6-bromo-2, 3-dihydro-1 H-inden-1 -ol (5.0 g, 23.47 mmol, 99percent). LC-MS m/z 195.0 (M-OH), 1.46 mm (ret. time).To a solution of 6-bromo-2, 3-dihydro-1H-inden-1-one (5 g, 23.69 mmol) in methanol (50 mL) was added sodium borohydride (0.896 g, 23.69 mmol) under NTo a solution of 6-bromo-2, 3-dihydro-1H-inden-1-one (5 g, 23.69 mmol) in methanol (100 mL) was added sodium borohydride (0.986 g, 26.1 mmol) under N2. The reaction mixturewas stirred at ambient temperature for 2 hrs. The solvent was removed by reducedpressure. The residue was re-dissolved in 100 mL of ethyl acetate and 20 mL of iN HCI.The organic layer was separated and the aqueous layer was extracted with ethyl acetate(3x). The combined organic layer was washed with brine and dried over anhydrous Na2SO4.After filtration and concentration, the title compound 6-bromo-2, 3-dihydro-1 H-inden-1 -ol (4.9g, 23.0 mmol, 97percent) was obtained and was carried over to next step without furtherpurification. LC-MS mlz 197.0 (M+H-18), 1.80 mm (ret. time)Under NUnder NTo a solution of 6-bromoindan-1-one (Aldrich, cat No.597147: 250 mg, 1.2 mmol) in methanol (3 mL) was added sodium tetrahydroborate (49 mg, 1.3 mmol) in 2 portions.

Molecular Weight:213.07
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:211.98368
Monoisotopic Mass:211.98368
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:149
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes