Bis(2-bromoethyl) ether → HCID 67099953, compound

A mixture of ethyl 2-(3-chloro-2-iodophenyl)acetate (1.3 g, 4.0 mmol) in 6 mL DMF was stirred at room temperature and treated with sodium hydride (0.23 g, 10 mmol). The mixture turned orange, was stirred for 10 minutes, and was treated with 1-bromo-2-(2-bromoethoxy)ethane (1.2 g, 5.2 mmol) in 6 mL DMF dropwise. The mixture was then stirred at room temperature for 2.5 hours. The mixture was carefully quenched with 20 mL H2O and 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. The crude product was purified by column eluting with (10-20% EtOAc/hexane) to give the title compound in 0.57 g. MS m/e: (M+H)+ 395.

1. stirringwas stirred for 10 minutes
2. stirringThe mixture was then stirred at room temperature for 2.5 hours
3. customThe mixture was carefully quenched with 20 mL H2O
4. extractionextracted with ether (3×100 mL)
5. washThe combined organic layers were washed with water (3×50 mL), 20 mL saturated NaCl
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated
8. customThe crude product was purified by column
9. washeluting with (10-20% EtOAc/hexane)

ORD record

ord-6b747e2f7b614e908baa887ae673964f

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2