Sulfuric Acid → 3-Bromo-2-fluorothioanisole

To a solution of 1-bromo-2-fluorobenzene (2.0 g, 11.4 mmol) in dry tetrahydrofuran (50 ml) under nitrogen, at −78° C. was added lithium diisopropylamide (2.5 M in hexane, 6.28 ml, 15.4 mmol). The mixture was stirred for 5 minutes after which dimethyldisulfide (0.92 ml, 15.4 mmol) was added and the stirring was continued at −78° C. for an additional hour. The reaction mixture was brought to ambient temperature and aqueous sulfuric acid (10%, 50 ml) was added. The phases were separated and the aqueous phase extracted with ethylacetate (3×100 ml). The combined organic phases was dried (MgSO4) and evaporated to dryness to give an oil. The residue was purified by flash column chromatography (isooctane) to give the title compound (1.26 g). MS m/z (relative intensity, 70 eV) 222 (M+, bp), 220 (M+, 91), 189 (24), 187 (25), 126 (97).

1. additionwas added
2. waitthe stirring was continued at −78° C. for an additional hour
3. customwas brought to ambient temperature
4. customThe phases were separated
5. extractionthe aqueous phase extracted with ethylacetate (3×100 ml)
6. dry with materialThe combined organic phases was dried (MgSO4)
7. customevaporated to dryness
8. customto give an oil
9. customThe residue was purified by flash column chromatography (isooctane)

ORD record

ord-1ed124e1cc9f4c6dbe5a76f5c4e55152

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763639B2