Diethyl Ether → 1-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Temperature

70 °C

To a mixture of 4-bromophenylacetonitrile (5.0 g, 25.44 mmol) and benzyltriethylammonium chloride (144.9 mg, 0.63 mmol) was added 1,2-dibromoethane (7.45 mL, 86.5 mmol). The reaction mixture was heated to 70° C. followed by dropwise addition of 50% aqueous sodium hydroxide solution (25 mL). The reaction mixture was heated at 70° C. for 7 h and then heated at 150° C. for 15 h. After the completion of reaction as confirmed by TLC, the reaction mixture was diluted with diethyl ether (100 mL). The aqueous layer was separated and acidified with 50% aqueous HCl to pH 1. The crude compound was diluted with ethyl acetate (500 mL). The organic layer was separated, washed with water (2×10 mL), dried over Na2SO4 and concentrated to afford title compound (3.1 g, 51%) as a solid.

1. temperatureThe reaction mixture was heated at 70° C. for 7 h
2. temperatureheated at 150° C. for 15 h
3. customAfter the completion of reaction
4. customThe aqueous layer was separated
5. additionThe crude compound was diluted with ethyl acetate (500 mL)
6. customThe organic layer was separated
7. washwashed with water (2×10 mL)
8. dry with materialdried over Na2SO4
9. concentrationconcentrated

ORD record

ord-19efff77a05843238fff714ccaeed4e6

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018249B2