Chlorotrimethylsilane → Silane, [(2-bromophenyl)methoxy]trimethyl-

To a solution of 2-bromobenzyl alcohol (4.86 g, 26 mmol) in CH2Cl2 (80 mL) cooled to 0° C. was added Me3SiCl (3.12 g, 28.6 mmol), triethylamine (4.34 g, 31.2 mmol) and 4-N,N-dimethylaminopyridine (0.32 g, 2.6 mmol). The cooling bath was removed and the mixture was allowed to warm to room temperature and stirred whereupon reaction was determined by thin layer chromatography to be completed after 2 h. The solution was washed with 1N aqueous HCl (30 mL) H2O (30 mL) and saturated aqueous NaHCO3 (30 mL). The organic phase was dried (MgSO4) and concentrated under vacuum to provide a brown oil, 6.67 g. Purification by column chromatography (80 g SiO2 eluted with 10% diethyl ether/hexane) afforded the product of Step A as a clear, yellow oil, 5.94 g, (88%); IR (neat): 2956, 2897, 1441, 1251 cm-1 ; 1H NMR (CDCl3); δ7.5 (dd, 2h), 7.3 (t,1H), 7.1 (t,1H), 4.7 (s,2H), 0.2 (s,9H).

1. customThe cooling bath was removed
2. washThe solution was washed with 1N aqueous HCl (30 mL) H2O (30 mL) and saturated aqueous NaHCO3 (30 mL)
3. dry with materialThe organic phase was dried (MgSO4)
4. concentrationconcentrated under vacuum
5. customto provide a brown oil, 6.67 g
6. customPurification
7. washby column chromatography (80 g SiO2 eluted with 10% diethyl ether/hexane)

ORD record

ord-8e2c88fddc7640389f386a1030ea295f

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USH0001401