Benzyl 3-bromopropyl ether

Clear colorless to yellow liquid

General procedure: To an open oven-dried reaction vial charged with a stir bar was added copper catalyst (2 mg, 0.002 mmol, 0.01 equiv), the alcohol (0.20 mmol, 1.0 equiv), carbon tetrabromide (131.6 mg, 0.4mmol, 2.0 equiv) and sodium bromide (41 mg, 0.40 mmol, 2.0 equiv). The flask vial was capped, purged with a stream of nitrogen and dry DMF (1.5 mL) was added via syringe. The reactionmixture was stirred under purple LEDs (394 nm) for 24 h. The vessel was opened and the mixturewas poured into a separatory funnel containing Et2O (10 mL) and H2O (10 mL). The layers wereseparated, and the aqueous layer was extracted with Et2O (2 × 10 mL). The combined organiclayers were washed with sat. Na2S2O3 solution, brine, dried over Na2SO4 and concentrated invacuo. The residue was purified by chromatography (100 percent hexanes)(3-Benzyloxy)-l-bromo-propane (2)PPhTriphenylphosphine was added in portion-wise to a cooled solution of 3-(benzyloxy)propan-1-ol (18.0 g, 0.108 mol), carbon tertabromide (44.76 g, 0.135 mol) in dichloromethane (270 mL) at 0 °C. Reaction was stirred for 20 h at ambient temperature. Reaction mixture was evaporated under vacuum and obtained solid was extracted with hexane (5*180 mL). The combined filtrate was evaporated under vacuum and crude was purified by column chromatography eluting 3-10percent ethyl acetate in hexane to get colorless liquid with 85percent yieldStep D(2): General procedure: To a 2 mL loop was loaded a solution with copper catalyst (0.002 mmol, 0.01 equiv), thealcohol (0.20 mmol, 1.0 equiv), carbon tetrabromide (131, 6 mg, 0.4 mmol, 2.0 equiv) andsodium bromide (41 mg, 0.40 mmol, 2.0 equiv) and 2 mL of dry DMF. The solution waspumped with a Syrris pump through two reactors of PFA tubing would around purpleLED strips for a total residence time of four hours and a flow rate 110 μL/min. The elutedreaction mixture was poured into a separatory funnel containing Et2O (10 mL) and H2O(10 mL). The layers were separated, and the aqueous layer was extracted with Et2O (2 ×10 mL). The combined organic layers were washed with sat. Na2S2O3 solution, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified bychromatography to afford the desired productGeneral procedure: To a 2 mL loop was loaded a solution with copper catalyst (0.002 mmol, 0.01 equiv), thealcohol (0.20 mmol, 1.0 equiv), carbon tetrabromide (131, 6 mg, 0.4 mmol, 2.0 equiv) andsodium bromide (41 mg, 0.40 mmol, 2.0 equiv) and 2 mL of dry DMF. The solution waspumped with a Syrris pump through two reactors of PFA tubing would around purpleLED strips for a total residence time of four hours and a flow rate 110 μL/min. The elutedreaction mixture was poured into a separatory funnel containing Et2O (10 mL) and H2O(10 mL). The layers were separated, and the aqueous layer was extracted with Et2O (2 ×10 mL). The combined organic layers were washed with sat. Na2S2O3 solution, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified bychromatography to afford the desired product

Can be effectively used for total synthesis of zincophorin and (+)-toxoid-a

Molecular Weight:229.11
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:5
Exact Mass:228.01498
Monoisotopic Mass:228.01498
Topological Polar Surface Area:9.2
Heavy Atom Count:12
Complexity:100
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes