Chemical Properties
Clear colorless to yellow liquid
Uses
Benzyl 3-bromopropyl ether may be used in the studies of preparation of (2S,3S)-1-[(triisopropylsilyl)oxy]-7-(benzyloxy)-2,3-(isopropylidenedioxy)-4(Z)-heptene, Ppeparation of 5-(3-Benzyloxypropoxy)psoralen (PAP-7), total synthesis of zincophorin and (+)-anatoxin-a.
General Description
Benzyl 3-bromopropyl ether is an ether.
Synthesis
GENERAL STEPS: To a dry reaction flask equipped with a magnetic stirrer under nitrogen protection, copper catalyst (2 mg, 0.002 mmol, 0.01 equiv), 3-benzyloxy-1-propanol (0.20 mmol, 1.0 equiv), carbon tetrabromide (131.6 mg, 0.4 mmol, 2.0 equiv) and sodium bromide (41 mg. 0.40 mmol, 2.0 equiv). The reaction vial was sealed and anhydrous DMF (1.5 mL) was added using a syringe. The reaction mixture was stirred under the light of a purple LED (394 nm) for 24 hours. Upon completion of the reaction, the mixture was transferred to a dispensing funnel and extracted by adding ether (10 mL) and water (10 mL). The organic phase was separated and the aqueous phase was further extracted with ether (2 x 10 mL). The organic phases were combined and washed sequentially with saturated aqueous NaHCO3 solution, Na2S2O3 solution and brine, dried with anhydrous Na2SO4 and concentrated under reduced pressure. Finally, the target product 3-benzyloxypropyl bromide was purified by silica gel column chromatography (100% hexane).
References
[1] Journal of the American Chemical Society, 2008, vol. 130, # 18, p. 6018 - 6024
[2] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 2730 - 2736
[3] Patent: WO2008/157726, 2008, A1. Location in patent: Page/Page column 220
[4] Tetrahedron Letters, 2016, vol. 57, # 13, p. 1486 - 1488
[5] Journal of the American Chemical Society, 1982, vol. 104, # 4, p. 1054 - 1068
