Hydrochloric Acid → HCID 57723635, compound

To a solution of 54.1 g (0.178 mol) of 4,7-dibromo-2-methyl-1-indanone in 240 ml of THF-methanol (2:1, vol.), 9.40 g (0.248 mmol) of NaBH4 was added in small portions for 2 hours at −5° C. (Caution: temperature must be lower 0° C.). The mixture was stirred overnight at ambient temperature. The resulting mixture was acidified with 10% HCl to pH=4. The organic layer was separated; the aqueous layer was extracted with 3×200 ml of methyl-tert-butyl ether. The combined organic fractions were dried over K2CO3 and evaporated to dryness. To the residue 500 ml of toluene were added. This toluene solution was treated with 50.0 g pTolSO3H for 5 hours at reflux. The resulting mixture was cooled to room temperature and passed through a short Silica Gel 60 column (40-63 μm, d 60 mm, l 40 mm). This column was additionally eluted with 700 cm3 of toluene. The combined extract was evaporated to dryness to give a white solid of the title product. Yield 47.2 g (92%).

1. customThe organic layer was separated
2. extractionthe aqueous layer was extracted with 3×200 ml of methyl-tert-butyl ether
3. dry with materialThe combined organic fractions were dried over K2CO3
4. customevaporated to dryness
5. additionTo the residue 500 ml of toluene were added
6. additionThis toluene solution was treated with 50.0 g
7. temperaturefor 5 hours at reflux
8. temperatureThe resulting mixture was cooled to room temperature
9. washThis column was additionally eluted with 700 cm3 of toluene
10. extractionThe combined extract
11. customwas evaporated to dryness

ORD record

ord-eb8ddbffc26949f89bf70899fa2bb71d

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550544B2