Dimethyl Disulfide → (2,6-Dimethyl-4-methylsulfanylphenoxy)triisopropylsilane

HRID 1171006Notes

Reaction equation

Br[C:2]1[CH:18]=[C:17]([CH3:19])[C:5]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])=[C:4]([CH3:20])[CH:3]=1.[Li]CCCC.[CH3:26][S:27]SC>C1COCC1>[CH3:19][C:17]1[CH:18]=[C:2]([S:27][CH3:26])[CH:3]=[C:4]([CH3:20])[C:5]=1[O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9]

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirring solution of (4-bromo-2,6-dimethylphenoxy)triisopropylsilane (0.5 g, 1.4 mmol) in THF (15 mL) at −78° C. was added n-BuLi (2.5 M in hexanes, 0.56 mL), the reaction mixture was stirred at −78° C. for 1 hr, then dimethyldisulfide (0.16 mL, 1.82 mmol) was added at −78° C. The reaction mixture was stirred at room temperature for 1 h and quenched with saturated NH4Cl and diluted with diethyl ether. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude (2,6-dimethyl-4-methylsulfanylphenoxy)triisopropyl-silane as an oil (0.46 g, 100%): 1H NMR (300 MHz, DMSO-d6): δ 6.92 (s, 2 H), 2.41 (s, 3 H), 2.20 (s, 6 H), 1.29 (m, 3 H), 1.10 (d, J=7.2 Hz, 18 H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase ethyl acetate-hexanes (2:98); Rf=0.57.

Workup

stirringThe reaction mixture was stirred at room temperature for 1 h
customquenched with saturated NH4Cl
additiondiluted with diethyl ether
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1cb8105d04f14c38bc96595055ee6e98
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829552B2

Reaction notes

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