Bis(2-bromoethyl) ether → Ethyl α-[2-(2-bromoethoxy)ethyl]-2-chloro-6-iodobenzeneacetate

A mixture of ethyl 2-(2-chloro-6-iodophenyl)acetate (4.5 g, 14 mmol) in 12 mL DMF was stirred at room temperature and treated with sodium hydride (0.80 g, 35 mmol). The mixture turned to orange and was stirred for 10 minutes. The mixture was treated dropwise with 1-bromo-2-(2-bromoethoxy)ethane (4.2 g, 18 mmol) in 12 mL DMF. The resulting mixture was stirred at room temperature for 2.5 hours. The reaction mixture was then warmed to 60° C. and stirred for 2 hours. The mixture was cooled to room temperature and quenched carefully with 20 mL H2O, extracted with ether (3×100 mL). The combined organic layers were washed with water (3×50 mL), 20 mL saturated NaCl, dried over anhydrous Na2SO4, and concentrated to give 5.8 g of the crude product as a yellow oil. MS m/e: (M+H)+ 475/477.

1. stirringwas stirred for 10 minutes
2. stirringThe resulting mixture was stirred at room temperature for 2.5 hours
3. temperatureThe reaction mixture was then warmed to 60° C.
4. stirringstirred for 2 hours
5. temperatureThe mixture was cooled to room temperature
6. customquenched carefully with 20 mL H2O
7. extractionextracted with ether (3×100 mL)
8. washThe combined organic layers were washed with water (3×50 mL), 20 mL saturated NaCl
9. dry with materialdried over anhydrous Na2SO4
10. concentrationconcentrated

ORD record

ord-575926ba3f894ecd847042de20e05ed1

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2