Dichlorodimethylsilane → (2-Methoxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilane

To a solution composed of tetrahydrofuran (31.5 ml), hexane (139 ml) and 1-bromo-3-tert-butyl-2-methoxy-5-methylbenzene (45 g) synthesized in the above-described procedure (2) was added a 1.6 mol/liter hexane solution (115 ml) of n-butyllithium dropwise at −40° C. over 20 minutes. The resultant mixture was kept at −40° C. for 1 hour, and tetrahydrofuran (31.5 ml) was then added dropwise. To a solution composed of dichlorodimethylsilane (131 g) and hexane (306 ml) was added the above-described mixture dropwise at −40° C. The resultant mixture was allowed to warm to room temperature over 2 hours, and further stirred at room temperature for 12 hours. The solvent and excess dichlorodimethylsilane were removed under reduced pressure from the reaction mixture, hexane-soluble components were extracted from the residue with hexane, and the solvent was distilled off from the resultant hexane solution to obtain 41.9 g of (3-tert-butyl-2-methoxy-5-methylphenyl)chlorodimethylsilane as a pale yellow oil. Yield was 84%.

1. customsynthesized in the above-described procedure (2)
2. additionwas added the above-described mixture dropwise at −40° C
3. customThe solvent and excess dichlorodimethylsilane were removed under reduced pressure from the reaction mixture, hexane-soluble components
4. extractionwere extracted from the residue with hexane
5. distillationthe solvent was distilled off from the resultant hexane solution

ORD record

ord-00e81cc6db584e048c326b0c827986c5

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06331593B1