Water → HCID 86729351, compound

(5-Bromo-2-sulfanylphenyl)methanol (0.50 g, 2.8 mmol) was dissolved in MeCN (11.4 mL) followed by the addition of water (11.4 mL) and solid potassium hydroxide (2.56 g, 45.6 mmol). The mixture was plunged into a −78° C. bath and when the mixture began to freeze diethyl[bromo(difluoro)methyl]phosphonate (1.22 g, 4.56 mmol) was added all at once and the cold bath was removed. The mixture was allowed to warm to ambient temperature and was stirred for 20 minutes. The mixture was then partitioned between EtOAc and water. The organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-25% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound. 1H NMR (500 MHz, CDCl3): δ 7.76 (s, 1H), 7.47 (m, 2H), 6.80 (t, J=56.5 Hz, 1H), 4.87 (s, 2H), 1.96 (br s, 1H).

1. customwas plunged into a −78° C.
2. additionwas added all at once and the cold bath
3. customwas removed
4. customThe mixture was then partitioned between EtOAc and water
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated in vacuo
8. customThe residue was purified by MPLC on silica gel (
9. washa gradient elution of 0-25% EtOAc/hexanes)
10. concentrationconcentrated in vacuo

ORD record

ord-ec8b35c512af42a7bcb85d922b2c84f9

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962608B2