4-Methoxybenzyl alcohol → 4-Methoxybenzyl 2-bromoacetate

To a -78° C. solution of p-methoxybenzyl alcohol (6.91 g, 50 mmol) and triethylamine (6.95 mL, 50 mmol) in anhydrous CH2Cl2 (50 mL) was added a solution of bromoacetyl bromide (10.1 g, 50 mmol) in CH2Cl2 at -78° C. under nitrogen, over a period of 10 min. The cooling bath was removed, and the reaction mixture was stirred for 2 h. The mixture was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated to provide 12 g (93% yield) of p-methoxybenzyl bromoacetate as a dark colored oil which was used in the next reaction without purification. A portion was purified by column chromatography on silica gel (elution with 20% ethyl acetate/hexanes) to give a clear, colorless oil. 1H NMR (300 MHz, CDCl3) δ3.79 (s, 3H), 3.83 (s, 2H), 5.12 (s, 2H), 6.87 (m, 2H), and 7.30 (m, 2H); IR (film) 1738 cm-1 ; MS (ESI/NH4OAc) M+NH4+ =276.

1. customThe cooling bath was removed
2. washThe mixture was washed with water and saturated sodium chloride solution
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated

ORD record

ord-baef67d864bb431796e9a0a96a3b5860

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05620969