3,4-Dichlorophenol → 1-Bromo-5-chloro-4-((3,4-dichlorophenoxy)methyl)-2-fluorobenzene

A mixture of 3,4 dichlorophenol (730 mg, 4.48 mmol), 1-bromo-4-(bromomethyl)-5-chloro-2-fluorobenzene (Preparation 2, 1.35 g, 4.48 mmol), and potassium carbonate (1.87 g, 13.5 mmol) in acetone (56 mL) was stirred for 72 hours at room temperature under a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate (100 mL) and filtered through Arbocel™. The Arbocel™ was washed with ethyl acetate (2×50 mL) and the combined organic extracts were concentrated in vacuo to afford a pale yellow solid. The solid was then dissolved in ethyl acetate (150 mL) and washed successively with aqueous sodium hydroxide solution (0.5 M, 100 mL), brine (3×100 mL), dried over sodium sulphate, filtered and concentrated in vacuo to afford an off white solid (1.90 g). Recrystallisation from hot heptane afforded the title compound (920 mg, 53%) as a white solid.

1. filtrationfiltered through Arbocel™
2. washThe Arbocel™ was washed with ethyl acetate (2×50 mL)
3. concentrationthe combined organic extracts were concentrated in vacuo
4. customto afford a pale yellow solid
5. washwashed successively with aqueous sodium hydroxide solution (0.5 M, 100 mL), brine (3×100 mL)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-0e3d6a6b7af0435d983cec2a67a28a03

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096500B2