Hydrochloric Acid → HCID 71230804, compound

Temperature

2.5 °C

To a mixture of 74.0 g (0.310 mol) of 7-bromo-2,4-dimethylindan-1-one and 5.86 g (0.155 mol) of NaBH4 in 310 ml of THF 155 ml of methanol was added dropwise by vigorous stirring for 5 h at 0-5° C. This mixture was stirred overnight at room temperature and then added to 1 liter of cold water. The resulting mixture was acidified by 2 M HCl to pH˜5, and then it was extracted with 3×250 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated. The resulting orange oil was dissolved in 600 ml of DMSO, then 70 g (1.25 mol) of KOH and 88 g (0.62 mol) of MeI were added to the resulting solution. This mixture was stirred for 3 h at ambient temperature. Further on, the solution was decanted from an excess of KOH, the latter was washed with 2×200 ml of dichloromethane, and 2000 cm3 of water was added to the combined solution. The organic layer was separated, and the aqueous layer was additionally extracted with 2×100 ml of dichloromethane. The combined organic extract was additionally washed with 5×1500 ml of water, dried over Na2SO4, and evaporated to dryness. Fractional distillation of the residue in vacuum gave 72.3 g (92%) of 7-bromo-1-methoxy-2,4-dimethylindane, b.p. 107-112° C./5 mm Hg.

1. additionwas added dropwise
2. stirringThis mixture was stirred overnight at room temperature
3. extractionit was extracted with 3×250 ml of dichloromethane
4. extractionThe combined organic extract
5. dry with materialwas dried over Na2SO4
6. customevaporated
7. dissolutionThe resulting orange oil was dissolved in 600 ml of DMSO
8. stirringThis mixture was stirred for 3 h at ambient temperature
9. customFurther on, the solution was decanted from an excess of KOH
10. washthe latter was washed with 2×200 ml of dichloromethane, and 2000 cm3 of water
11. additionwas added to the combined solution
12. customThe organic layer was separated
13. extractionthe aqueous layer was additionally extracted with 2×100 ml of dichloromethane
14. extractionThe combined organic extract
15. washwas additionally washed with 5×1500 ml of water
16. dry with materialdried over Na2SO4
17. customevaporated to dryness
18. distillationFractional distillation of the residue in vacuum

ORD record

ord-24c695c1e762456c857a7fe9c527a3f7

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187583B2