m-Chloroperbenzoic acid → HCID 12694925, compound

Temperature

2.5 °C

To a solution of 6-bromo-1,2-dihydronaphthalene (250 g, 1.20 mol) in dichloromethane (3.75 L) add saturated aqueous sodium bicarbonate (1250 mL) and cool to 0-5° C. Add MCPBA (77%, 275 g, 1.23 mol, 1.03 eq) in portions. Stir the mixture mechanically at 0-5° C. for 1.5 hr. and allow to warm to room temperature. Stir at room temperature for approximately 1.5 hr. and add additional MCPBA (77%, 15.0 g, 67 mmol, 0.05 eq) at room temperature and stir for approximately one hour. Dilute the mixture with dichloromethane (3750 mL) and separate the layers. Wash the organic layer with saturated aqueous sodium bicarbonate (3 L). Mix a 10% aqueous sodium bisulfate solution (3750 mL) with aqueous saturated sodium bicarbonate (1250 mL) to prepare a solution with a final pH of approximately 7. Add this solution to the dichloromethane layer and stir at room temperature for about 10 min. Separate the layers, wash the organic layer with saturated aqueous sodium bicarbonate (3 L) and brine (3 L). Concentrate in vacuo to obtain the title compound as an oil (263 g, 98%). GC/MS m/z (79Br/81Br) 224/226 [M+].

1. temperatureto warm to room temperature
2. stirringStir at room temperature for approximately 1.5 hr
3. stirringstir for approximately one hour
4. customseparate the layers
5. washWash the organic layer with saturated aqueous sodium bicarbonate (3 L)
6. additionMix a 10% aqueous sodium bisulfate solution (3750 mL) with aqueous saturated sodium bicarbonate (1250 mL)
7. customto prepare a solution with a final pH of approximately 7
8. stirringstir at room temperature for about 10 min
9. customSeparate the layers
10. washwash the organic layer with saturated aqueous sodium bicarbonate (3 L) and brine (3 L)
11. concentrationConcentrate in vacuo

ORD record

ord-61e5873c8b8741a8a0eb2fd29c6ba188

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08227468B2