m-Chloroperbenzoic acid → 2-(3-Bromophenyl)oxirane

A solution of 3-bromostyrene (1.0 g, 5.46 mmol) in CH2Cl2 (10 mL) was cooled in an ice bath. 3-Chloroperoxybenzoic acid (57% pure) (1.82 g, 6.01 mmol) was added in one batch and the stirring was continued over 18 h. The reaction mixture was concentrated to a residue and diluted with CCl4 (20 mL). Precipitated m-chlorobenzoic acid was removed by filtration and the filtrate was washed with a 50:50 mixture of 5% aq. NaHCO3 and 5% aq. NaHSO3 (100 mL). The organic extract was dried over Na2SO4 and concentrated under reduced pressure to yield 0.80 g (64%) of product as a yellow oil. 1H NMR (CDCl3) δ2.74 (m, 1, CH), 3.14 (m, 1, CH--), 3.82 (m, 1, --CH--), 7.21 (m, 2, phenyl), 7.42 (m, 2, phenyl).

1. concentrationThe reaction mixture was concentrated to a residue
2. additiondiluted with CCl4 (20 mL)
3. customPrecipitated m-chlorobenzoic acid was removed by filtration
4. washthe filtrate was washed with a 50:50 mixture of 5% aq. NaHCO3 and 5% aq. NaHSO3 (100 mL)
5. extractionThe organic extract
6. dry with materialwas dried over Na2SO4
7. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-47aa4e8a60a549c99d0bf2809cc4687b

Quelldatensatz

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05616575