2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(3,5-Dichloro-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1-Bromo-3,5-dichloro-2-methoxybenzene (Preparation 25, 4.4 g, 17.5 mmol) in 95 ml diethylether was cooled to −78° C. under nitrogen. tBuLi (10 ml, 35.16 mmol) was added dropwise and the reaction stirred for 15 minutes. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.58 g, 29 mmol) was added and the reaction stirred at −78° C. for 1 hour before pouring the reaction into 50 ml ice cold ammonium chloride (aqueous). The product was extracted with diethylether (3×30 ml), the combined organic layers were washed with water (50 ml) and brine (2×25 ml), dried over sodium sulphate, and concentrated in vacuo to afford a yellow oil. This was purified using silica gel column chromatography (heptane:ethyl acetate 9:1) to furnish a yellow oil, 4.5 g

1. stirringthe reaction stirred at −78° C. for 1 hour
2. additionbefore pouring
3. extractionThe product was extracted with diethylether (3×30 ml)
4. washthe combined organic layers were washed with water (50 ml) and brine (2×25 ml)
5. dry with materialdried over sodium sulphate
6. concentrationconcentrated in vacuo
7. customto afford a yellow oil
8. customThis was purified
9. customto furnish a yellow oil, 4.5 g

ORD record

ord-7692fa7235e5404faa3aa2f4434bee20

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572797B2