1-Bromo-2-Chloroethane → 1-(4-Bromo-2-trifluoromethyl-phenyl)-cyclopropanecarbonitrile

Temperature

50 °C

To a stirred solution of (4-bromo-2-trifluoromethyl-phenyl)-acetonitrile (3.33 g, 12.61 mmol) from step 2 of example A(141), benzyltriethylammonium chloride (0.057 g, 0.25 mmol) and 1-bromo-2-chloroethane (1.57 g, 10.94 mmol), was added dropwise a solution of NaOH 40% (3 mL). The reaction mixture was stirred 6 hours at 50° C. After this time the reaction was quenched with 1N HCl (30 mL) and extracted with EtOAC (3×30 mL). The organic phase was dried over Na2SO4 and evaporated. The crude organic product was purified by flash column chromatography (10% EtOAc in hexanes) to give the product (3.1 g, 86%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 1.4-1.44 (m, 2H), 1.76-1.80 (m, 2H), 7.44 (d, J=8.3 Hz, 1 H), 7.69 (dd, J=8.3, 2 Hz, 1 H), 7.84 (d, J=2 Hz, 1 H).

1. customAfter this time the reaction was quenched with 1N HCl (30 mL)
2. extractionextracted with EtOAC (3×30 mL)
3. dry with materialThe organic phase was dried over Na2SO4
4. customevaporated
5. customThe crude organic product was purified by flash column chromatography (10% EtOAc in hexanes)

ORD record

ord-b5bc15a3d3194529a0bda5ba90708fe7

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2