Bis(2-bromoethyl) ether → Ethyl 4-(4-fluorophenyl)-tetrahydro-2H-pyran-4-carboxylate

Temperature

0 °C

A mixture of NaH (1.7 g, 71 mmol) in 100 mL NMP stirred at 0° C., was treated dropwise with a mixture of ethyl 2-(4-fluorophenyl)acetate (5.2 g, 29 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (6.6 g, 29 mmol) in 20 mL ether. The mixture was allowed to warm to room temperature and stirred for 5 hours, M+1=253. The mixture was then carefully quenched with 100 mL H2O, and the pH was adjusted to 5. The mixture was extracted with ether (3×100 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (20 mL). The combined organic layers were then dried over anhydrous Na2SO4 and concentrated in vacuo to give 7.1 g of the crude product as a pale yellow oil. MS (m/z)=253 (M+H)+.

1. temperatureto warm to room temperature
2. stirringstirred for 5 hours
3. customThe mixture was then carefully quenched with 100 mL H2O
4. extractionThe mixture was extracted with ether (3×100 mL)
5. washThe combined organic layers were washed with H2O (3×50 mL) and brine (20 mL)
6. dry with materialThe combined organic layers were then dried over anhydrous Na2SO4
7. concentrationconcentrated in vacuo

ORD record

ord-ed51f6f0241c497f9c22514839cba7b0

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928139B2