Potassium Hydroxide → 1-Bromo-4-(cyclopropylmethyl)benzene

4-Bromophenyl cyclopropyl ketone (5.63 g), hydrazine monohydrate (2.5 ml) and potassium hydroxide (3.33 g) were added to ethylene glycol (25 ml) and the mixture heated to reflux for 1 hour. The reaction mixture was cooled and partitioned between water (20 ml) and ethyl acetate (30 ml) and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (30 ml) and the combined organic phases were washed with 2M hydrochloric acid (15 ml) and water (15 ml) then dried (MgSO4) and evaporated. The residue was purified by chromatography on a Mega Bond Elut column, eluting with hexane to give 1-bromo-4-(cyclopropylmethyl)benzene (2.6 g); 1H NMR (CDCl3): 0.2 (m, 2H), 0.55 (m, 2H), 2.50 (d, 2H), 7.14 (d, 2H), 7.41 (d, 2H); mass spectrum (EI+) 210 (M.)+.

1. temperaturethe mixture heated
2. temperatureto reflux for 1 hour
3. temperatureThe reaction mixture was cooled
4. custompartitioned between water (20 ml) and ethyl acetate (30 ml)
5. customthe organic layer was separated
6. extractionThe aqueous layer was extracted with ethyl acetate (30 ml)
7. washthe combined organic phases were washed with 2M hydrochloric acid (15 ml) and water (15 ml)
8. dry with materialthen dried (MgSO4)
9. customevaporated
10. customThe residue was purified by chromatography on a Mega Bond Elut column
11. washeluting with hexane

ORD record

ord-b0dc0e857a85423a8741b4e64ca2367c

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06258817B1