m-Chloroperbenzoic acid → 1-Bromo-3-(methanesulfinyl)benzene

Temperatur

0 °C

3-Bromothioanisol (0.5 g, 2.46 mmol) was added to methylene chloride (12 mL) and chilled to 0° C. To this was added 3-chloroperoxybenzoic acid (0.467 g, 2.71 mmol). The m-CPBA did not dissolve completely. The mixture was stirred overnight. The reaction was quenched with a saturated sodium thiosulfate (30 mL) solution. The product was extracted with EtOAc (3×20 mL). The organic fractions were combined, washed with brine (20 mL), and dried with sodium sulfate. The organic was then concentrated to yield 0.912 g (81%) 1-bromo-3-methanesulfinyl-benzene. 1HNMR (methylene chloride-d2) δ 7.83 (t, J=2.0 Hz, 1H), 7.66 (d, J=7.6 Hz, 1H), 7.57 (d, J=8.3 Hz, 1H), 7.44 (t, J=7.9 Hz, 1H), 2.77 (s, 3H); LC-MS RT: 1.28, [M+H]+: 219.0.

1. customThe reaction was quenched with a saturated sodium thiosulfate (30 mL) solution
2. extractionThe product was extracted with EtOAc (3×20 mL)
3. washwashed with brine (20 mL)
4. dry with materialdried with sodium sulfate
5. concentrationThe organic was then concentrated

ORD-Eintrag

ord-a0ee4c34218841dc80614d4decb5817c

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07420066B2