Water → 4-{[(3-Chloro-4-hydroxyphenyl)thio]methyl}benzaldehyde

Triethylamine (5.0 mL, 35.9 mmol) was added dropwise to a solution of 2-chloro-4-mercaptophenol (3.60 g, 22.4 mmol) and 4-bromomethyl benzaldehyde (3.93 g, 19.7 mmol) in dioxane (150 mL) at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 20 hours. Water (100 mL) was added to the reaction mixture and it was then partitioned with ethyl acetate and brine (200 mL each). The aqueous layer was re-extracted with ethyl acetate (100 mL). The combined organic layers were dried over sodium sulphate and concentrated in vacuo affording a yellow solid. This was purified by trituration with acetonitrile (5 mL/g) for 30 minutes. After filtration this afforded a light yellow solid as the pure product, 84% yield, 5.27 g.

1. customwas then partitioned with ethyl acetate and brine (200 mL each)
2. extractionThe aqueous layer was re-extracted with ethyl acetate (100 mL)
3. dry with materialThe combined organic layers were dried over sodium sulphate
4. concentrationconcentrated in vacuo
5. customaffording a yellow solid
6. customThis was purified by trituration with acetonitrile (5 mL/g) for 30 minutes
7. filtrationAfter filtration
8. customthis afforded a light yellow solid as the pure product, 84% yield, 5.27 g

ORD 기록

ord-baf0fbcee31e48baaab346ce0d70e562

출처 데이터셋

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08822439B2