Water → HCID 59832511, compound

To a solution of 12.6 g (40.0 mmol) of 1,3,5-tribromobenzene in 400 ml of ether, 160 ml (40.0 mmol) of 0.25 M nBuLi in hexanes was added for 1 h at −80° C. The mixture was stirred for 1.5 h at this temperature, and then a solution of 5.29 g (40.0 mmol) of indanone-2 in 200 ml of ether was added dropwise over 1 hour while vigorously stirring. The reaction mixture was allowed to warm to room temperature and it was stirred at this temperature for 24 h. Then, 100 ml of water was added. The organic layer was separated; the aqueous layer was extracted with 3×50 ml of dichloromethane. The combined organic layers were dried over Na2SO4 and then evaporated to dryness. The residue was dissolved in 250 ml of toluene, and 0.75 g of p-TosOH was added. The resulting solution was refluxed for 1 hours using a Dean-Stark trap to remove the water formed. Next, the mixture was evaporated to dryness, and the product was isolated by flash-chromatography on Silica Gel 60 (d 50 mm, 1 400 mm, eluent: hexanes). Yield 8.54 g (61%) of white powder.

1. stirringwhile vigorously stirring
2. stirringit was stirred at this temperature for 24 h
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with 3×50 ml of dichloromethane
5. dry with materialThe combined organic layers were dried over Na2SO4
6. customevaporated to dryness
7. dissolutionThe residue was dissolved in 250 ml of toluene
8. addition0.75 g of p-TosOH was added
9. temperatureThe resulting solution was refluxed for 1 hours
10. customto remove the water
11. customformed
12. customNext, the mixture was evaporated to dryness
13. customthe product was isolated by flash-chromatography on Silica Gel 60 (d 50 mm, 1 400 mm, eluent: hexanes)

ORD record

ord-fb12c564d0754a2686719df5a61658b2

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538168B2