Methyl iodide → HCID 59386539, compound

Temperature

5 °C

To a solution of 100 g (0.474 mol) of 4-bromo-1-indanone in 530 ml of THF-methanol (2:1, vol.), 26.8 g (0.709 mol) of NaBH4 was added in small portions at vigorous stirring for 1.5 hours at 5° C. This mixture was stirred at room temperature for 12 hours and then added to 1 L of cold water. The hydrogenation product was extracted with 4×200 ml of dichloromethane, and the combined extract was evaporated to dryness. To 108 g (1.93 mol) of KOH in 700 ml of DMSO, 135 g (59.2 ml, 0.948 mol) MeI, and a solution of crude 4-bromoindan-1-ol in 300 ml of DMSO were added. This mixture was stirred for 2 hours at ambient temperature; then, 67.2 g (29.5 ml, 0.473 mol) of MeI was added, and the mixture was additionally stirred for 2 hours. The resulting mixture was added to 2 L of cold water. The crude product was extracted with 5×200 ml of dichloromethane. The combined extract was dried over Na2SO4 and, then, evaporated to dryness. Fractional distillation gave 4-bromo-1-methoxyindane, b.p. 94° C./2 mm Hg. Yield, 100 g (93%) of a colorless oil.

1. stirringThis mixture was stirred at room temperature for 12 hours
2. extractionThe hydrogenation product was extracted with 4×200 ml of dichloromethane
3. extractionthe combined extract
4. customwas evaporated to dryness
5. stirringThis mixture was stirred for 2 hours at ambient temperature
6. stirringthe mixture was additionally stirred for 2 hours
7. extractionThe crude product was extracted with 5×200 ml of dichloromethane
8. extractionThe combined extract
9. dry with materialwas dried over Na2SO4
10. customevaporated to dryness
11. distillationFractional distillation

ORD record

ord-6b51593080ae44459fd95325346de665

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763562B2