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-5f47a10815de490f8543c84dcf897031

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748451B2