1,3-Dibromopropane → 1-(4-Bromophenyl)cyclobutanecarbonitrile

Temperature

100 °C

A solution of potassium hydroxide (56.5 g) and tetrabutylammonium bromide (2.92 g) in toluene (400 mL) and water (30 mL) was warmed to 70° C. Then, 1,3-dibromopropane (39.0 g) and 2-(4-bromophenyl)acetonitrile (35.5 g) were sequentially added thereto, and the mixture was stirred at 100° C. for 3 hours. After the reaction mixture was cooled to 80° C., heptane (100 mL) was added thereto, and the mixture was further cooled to room temperature. The reaction mixture was filtered and washed with hexane, and the organic layer was separated. The obtained organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate) to give the desired product (24.0 g, yield: 56%) as a colorless oil.

1. temperatureAfter the reaction mixture was cooled to 80° C.
2. temperaturethe mixture was further cooled to room temperature
3. filtrationThe reaction mixture was filtered
4. washwashed with hexane
5. customthe organic layer was separated
6. washThe obtained organic layer was washed with saturated sodium chloride
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate)

ORD record

ord-c44fea2a886349d38e60d6245599d60f

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09375434B2