Ethylene Glycol → 2-((4-Bromobenzyl)oxy)ethanol

Temperature

60 °C

Ethylene glycol (0.084 mL, 1.5 mmol) was added to NaH (38 mg, 1.52 mmol, 95% in oil) in THF (3 mL). 1-Bromo-4-(bromomethyl)benzene (370 mg, 1.5 mmol) was added to the reaction, and the residual 1-bromo-4-(bromomethyl)benzene was transferred to the reaction tube with additional THF (1 mL). (Bu)4NI (55 mg, 0.15 mmol) was then added, and the reaction was heated at 60° C. for 18 h and then rt for 4 h. H2O (2 mL) and EtOAc (2 mL) were added, and the layers were separated via pipette. The aqueous layer was extracted with EtOAc (1×1 mL), and the combined organic layers were concentrated. The crude product was purified on a SPE cartridge (5 g silica) eluting with the following 10 mL fractions: 30% EtOAc/hexanes (fractions 1,2), 50% EtOAc/hexanes (fraction 3), and 75% EtOAc/hexanes (fraction 4) to give the title compound (139 mg, 40%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

1. customthe layers were separated via pipette
2. extractionThe aqueous layer was extracted with EtOAc (1×1 mL)
3. concentrationthe combined organic layers were concentrated
4. customThe crude product was purified on a SPE cartridge (5 g silica)
5. washeluting with the following 10 mL fractions

ORD record

ord-26e9dfa79aaf450c83e60fc284a6ccce

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183257B2