3,5-Dichlorophenol → Tert-butyl(3,5-dichlorophenoxy)dimethylsilane

Participants

Reaction Steps

To a solution of CH2Cl6 (60 mL) and 3,5-dichlorophenol (5.0 g 30 mmol) was added tert-butyldimethylsilyl chloride (5.54 g, 36 mmol), N,N-diisoprpylethylamine (8.0 mL, 46 mmol) and a catalytic amount of 4-dimethylaminopyridine. The initially exothermic solution was stirred at ambient temperature for 6 h then diluted with CH2Cl2 (40 mL). The mixture was washed consecutively with 10% aqueous HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL). the organic phase was dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide 13 as a pale yellow liquied (8.8 g, 100%). 1H NMR (300 MHz, CDCl3) d 6.98 s, 1H), 6.72 (s, 2H), 0.98 (s, 9H), 0.22 (s, 6H).

Provenance & Evidence