Thionyl Chloride → 4-Bromo-1-(chloromethyl)-2-methylbenzene

(4-Bromo-2-methyl-phenyl)-methanol (40.0 g, 199 mmol) was added to thionyl chloride (106.6 g, 0.896 mole, 65.3 mL). The mixture was heated to reflux, for 1.5 hours. After cooling to room temperature the mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc (300 mL) and added carefully to saturated aqueous NaHCO3 (500 mL). The EtOAc layer was separated, and the aqueous layer was extracted with EtOAc (250 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo yielding the title compound (34.19 g, 157 mmol, 79%) as a slightly colored oil that solidified to a white solid upon standing. 1H NMR (CDCl3, 300 MHz) δ ppm 2.38 (s, 3H); 4.57 (s, 2H); 7.12 (d, 1H); 7.28 (s, 1H); 7.55 (d, 1H)

1. temperatureThe mixture was heated
2. temperatureto reflux, for 1.5 hours
3. concentrationwas concentrated under reduced pressure
4. dissolutionThe residue was dissolved in EtOAc (300 mL)
5. additionadded carefully to saturated aqueous NaHCO3 (500 mL)
6. customThe EtOAc layer was separated
7. extractionthe aqueous layer was extracted with EtOAc (250 mL)
8. dry with materialThe combined organic layers were dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-1f783c5dbae74ef3a480d0a946399117

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853258B2