3,4-DIMETHOXYBENZYL BROMIDE

General procedure: benzyl alcohols (1 mmol) in dry benzene (15 mL) and phosphorus tribromides (0.5 mL) and stirred at room temperature to get respective benzyl bromides in quantitative yields, usual work-up.General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P4-Bromomethyl-1.2-dimethoxybenzene To 3, 4-dimethoxybenzyl alcohol (1680 mg, 10.0 mmol) in 20ml CHTo a flame dried flask cooled under argon was added (3, 4-dimethoxyphenyl)methanol (0.169 grams, 1.0 mmol, 1.0M in dichloromethane, stored over 4 angstrom molecular sieves, purchased from Fisher Scientific). To a solution of 3, 4-dimethoxybenzyl alcohol (10 g, 59.5 inmol) , carbon tetrabromide (22 g, 65.4 iranol) , and THF(250 mL) was added triphenylphosphine (17 g, 65.4 mmol) inTHF (75 mL) . The reaction was heated at 60 °C for 1 h andconcentrated to an oil. To the residue was added 1:1 .CH2Cl2:Et20 and the resulting solid was filtered. Thefiltrate was concentrated and chromatographed on florisilwith CHIn a 100 mL round-bottomed flask, 4D (2 g, 12.0 mmol) was added and dissolved in methanol (30 mL). Sodium borohydride (454 mg, 12.0 mmol) was added in portions at room temperature. The reaction was continued for 1 h at room temperature and the reaction solution was concentrated to a small volume. , Water and ethyl acetate were added to separate the layers. The organic phase was collected, dried over anhydrous sodium sulfate, and spin-dried to give 4E as a colorless oil.The 4E was dissolved in diethyl ether (25 mL) and phosphorous tribromide (712 μL, 7.50 mmol) was added dropwise at room temperature. The addition was complete and the reaction was carried out at room temperature for 1 h.The reaction solution was placed in an ice bath, saturated sodium bicarbonate was added to quench the reaction, and the mixture was further extracted with ethyl acetate, dried over anhydrous sodium sulfate, and spin-dried to obtain white solid 4F (1.48 g, yield 53.4percent).

Reagent used in the dimethoxybenzyl alkylations.

Molecular Weight:231.09
XLogP3:2.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:229.99424
Monoisotopic Mass:229.99424
Topological Polar Surface Area:18.5
Heavy Atom Count:12
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes