Tetrahydrofuran → 6-Bromo-1-methylene-indan

6-Bromo-indan-1-one 38b (898 mg, 4.25 mmol) was dissolved in 5 mL of tetrahydrofuran under stirring followed by addition of above mentioned mixture. The reaction mixture was stirred at room temperature for 1 hour prior to quenching by addition of 25 mL of water. The mixture was extracted with dichloromethane (25 mL×4). The combined organic extracts were washed with saturated brine (10 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 6-bromo-1-methylene-indan 38c (830 mg, yield 93.4%) as a yellow oil.

1. additionfollowed by addition
2. stirringThe reaction mixture was stirred at room temperature for 1 hour
3. customto quenching by addition of 25 mL of water
4. extractionThe mixture was extracted with dichloromethane (25 mL×4)
5. washThe combined organic extracts were washed with saturated brine (10 mL×2)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-899b82314e884d73b6c30ffac8ea0512

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2