Methanol → Methyl 4-(2-bromoethyl)benzoate

Temperature

0 °C

4-(2-Bromo-ethyl)-benzoic acid (1.00 g, 4.37 mmol) was dissolved in MeOH (10 mL) and cooled to 0° C. This was followed by dropwise addition of thionyl chloride (0.48 mL, 6.55 mmol). The mixture was refluxed for 2 h, followed by removal of all volatiles by rotary evaporation. The resulting oil was taken up in EtOAc (50 mL) and washed with water (50 mL). The EtOAc portion was separated, dried (Na2SO4) and concentrated to give the product (1.04 g, 98%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.00 (d, 2H, J=6.54 Hz), 7.29 (d, 2H, J=7.1 Hz), 3.92 (s, 3H), 3.59 (t, 2H, J=7.38 Hz), 3.23 (t, 2H, J=7.34 Hz).

1. temperatureThe mixture was refluxed for 2 h
2. customfollowed by removal of all volatiles by rotary evaporation
3. washwashed with water (50 mL)
4. customThe EtOAc portion was separated
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated

ORD record

ord-1284aba7ff824f7f9994c7f83c8b35e1

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431538B2