Dimethylformamide → 1-Bromo-3-[(methylsulfanyl)methyl]benzene

Temperature

0 °C

Sodium thiomethoxide (0.616 g, 8.8 mmol) was added to DMF (8 mL) and cooled to 0° C. To this solution was added 1-bromo-3-bromomethyl-benzene (2 g, 8 mmol). The mixture was allowed to warm to rt and stir for 18 h. The mixture was then poured into cold water (50 mL) and extracted with EtOAc (3×20 mL). The organics were combined and dried with sodium sulfate. The solution was concentrated in vacuo to yield the crude product, which was then purified via flash chromatography (5% ethyl acetate—hexanes) to yield 1.3 g (68.5%) of 1-bromo-3-methylsulfanylmethyl-benzene as a pure product. 1H-NMR (methylene chloride -d2) δ 7.48-7.47 (m, 1H), 7.392 (dt, J=7.9, 1.5 Hz, 1H), 7.28-7.207 (m, 2H), 3.64 (s, 2H), 1.99 (s, 3H); LC-MS RT: 3.70, [M+H]+: 354.1.

1. temperatureto warm to rt
2. extractionextracted with EtOAc (3×20 mL)
3. dry with materialdried with sodium sulfate
4. concentrationThe solution was concentrated in vacuo
5. customto yield the crude product, which
6. customwas then purified via flash chromatography (5% ethyl acetate—hexanes)

ORD record

ord-77ce376a03ca4adfa5ba89fc5f893677

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07420066B2