Carbon tetrabromide → 1-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzene

Temperature

-10 °C

To a solution of (2-bromo-5-(trifluoromethyl)phenyl)methanol (4.7 g, 18 mmol) in methylene chloride (50 mL) at −10° C. was added carbon tetrabromide (CBr4) (7.17 g, 21.6 mmol). The resulting mixture was stirred at −10° C. for 15 minutes. Triphenylphosphine (5.61 g, 21.4 mmol) was then slowly added portionwise. This mixture was stirred at room temperature for 16 hours. The mixture was partitioned between saturated ammonium chloride (NH4Cl) (50 ml) and methylene chloride (2×50 mL). The combined organic layers were washed with saturated NaCl (50 mL), dried (MgSO4) and concentrated. The residue was purified by flash chromatography (silica gel) (eluted with 3:1 hexanes-ethyl acetate) to yield the title compound as a white solid (4.01 g). 1H NMR (400 MHz, CDCl3) δ 4.6 (s, 2H) 7.5 (dd, J=8.3, 1.6 Hz, 1H) 7.8 (m, 2H).

1. stirringThis mixture was stirred at room temperature for 16 hours
2. customThe mixture was partitioned between saturated ammonium chloride (NH4Cl) (50 ml) and methylene chloride (2×50 mL)
3. washThe combined organic layers were washed with saturated NaCl (50 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customThe residue was purified by flash chromatography (silica gel) (eluted with 3:1 hexanes-ethyl acetate)

ORD record

ord-301daa5019ac463bb51218ea12bbb7ec

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919506B2