4-Bromo-2-chloro-thiobenzoic acid S-pyridin-2-yl Ester → 1-(4-Bromo-2-chlorophenyl)ethan-1-one

4-Bromo-2-chloro-thiobenzoic acid S-pyridin-2-yl ester (1.86 g, 5.66 mmol) from Step 1 above was dissolved in dry THF (30 mL) and cooled to −78° C. A solution of methyl magnesium bromide in 75:25 toluene/THF (1.4 M, 4.45 mL, 6.23 mmol) was added dropwise. After stirring 35 min, the cooling bath was removed. The reaction mixture was quenched with saturated 1N HCl and extracted with EtOAc (30 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4 and evaporated. The residue was purified by flash column chromatography (10% EtOAc in hexanes) to give the product (1.05 g, 80%) as a colorless oil. 1H NMR (CDCl3) δ 2.64 (s, 3H), 7.46-7.48 (m, 2H), 7.61 (s, 1H).

1. customthe cooling bath was removed
2. customThe reaction mixture was quenched with saturated 1N HCl
3. extractionextracted with EtOAc (30 mL)
4. washThe organic phase was washed with brine (50 mL)
5. dry with materialdried over Na2SO4
6. customevaporated
7. customThe residue was purified by flash column chromatography (10% EtOAc in hexanes)

ORD-Eintrag

ord-e5e3f9e8a0ed4f3d842396cfc4f94665

Quelldatensatz

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07473790B2