Chlorotrimethylsilane → HCID 21707576, compound

Participants

Reaction Conditions

Reaction Steps

A flame-dried 3-necked flask was charged with 2,4-difluoro-1-methoxymethylphenol (26, 0.84 g, 4.8 mmol) in 30 mL of freshly distilled THF under argon and this mixture was cooled to -78° C. (FIG. 2E). nBuLi (2.5 M solution in hexane, 2.2 mL, 5.43 mmol) was added to this reaction mixture which was allowed to stir at -78° C. for 2.5 hours under argon. Chlorotrimethyl silane (1.0 M solution in THF, 5.43 mL, 5.43 mmol) was then added to the deep pink colored mixture at -78° C. and then the acetone/dry ice bath was removed and the reaction was allowed to proceed at room temperature for 14 h. Sat. NH4Cl (~20 mL) was added to the mixture which was then stirred for an additional 10 minutes and then extracted with ethyl ether (3×10 mL). The combined organic solution was washed with brine, water and then dried (MgSO4) and filtered. The solvent was removed under vacuo to afford the crude product which was purified by flash chromatography on silica gel (EtOAc:hexanes; 5:95) to yield a yellow oil (0.8 g, 79%). 1H NMR (CDCl3) δ 7.09-7.17 (m, 1H, ArH), 6.68-6.74 (m, 1H, ArH), 5.13 (s, 2H, CH2), 3.52 (s, 3H, CH3), 0.36-0.37 (t, 9H, Si(CH3)3); FAB-MS 247 (MH+, 70), 229 (40), 219 (60), 189 (58), 157 (40), 133 (60), 79 (100).

Provenance & Evidence