Water → HCID 68507957, compound

Temperature

1 °C

(S)-5-Bromo-indan-2-carboxylic acid (12.65 mmol) was dissolved in dry THF (75 mL). The mixture was cooled with stirring to 0-2° C. under argon. 1M BH3 in THF (18.4 mL; 18.4 mmol) was added via syringe at a rapid dropwise rate. The mixture was stirred at 0° C. for 30 minutes then allowed to warm to rt and stir for 90 minutes. The reaction mixture was cooled again to 0° C. and treated carefully with 10 mL of water. Volatiles were removed under reduced pressure and the residue partitioned between diethyl ether (100 mL) and brine (50 mL). The aqueous phase was extracted with 100 mL ethyl ether and each extract washed with brine. The combined extracts were dried over Na2SO4, filtered and volatiles were removed under reduced pressure to give 2.85 g of ((S)-5-bromo-indan-2-yl)-methanol as a crystalline white solid.

1. temperatureThe mixture was cooled
2. stirringThe mixture was stirred at 0° C. for 30 minutes
3. temperatureto warm to rt
4. stirringstir for 90 minutes
5. temperatureThe reaction mixture was cooled again to 0° C.
6. customVolatiles were removed under reduced pressure
7. customthe residue partitioned between diethyl ether (100 mL) and brine (50 mL)
8. extractionThe aqueous phase was extracted with 100 mL ethyl ether
9. washeach extract washed with brine
10. dry with materialThe combined extracts were dried over Na2SO4
11. filtrationfiltered
12. customvolatiles were removed under reduced pressure

ORD record

ord-0d1cd795e892459293430bf41c6d1d56

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803816B2