Water → 2-Methyl-5-(trimethylsilyl)phenoxytrimethylsilane

HRID 2217094Notes

Reaction equation

HRID 2217094 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.C([Li])CCC.[CH3:15][Si:16](Cl)([CH3:18])[CH3:17].O>C1COCC1>[CH3:9][C:5]1[CH:4]=[CH:3][C:2]([Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:7][C:6]=1[O:8][Si:16]([CH3:18])([CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 126484045-Bromo-2-methylphenol2×HCID 178418339Butyllithium

Product 1

HCID 598248302-Methyl-5-(trimethylsilyl)phenoxytrimethylsilaneYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-2-methylphenol (Intermediate 1, 3.6 g, 19.3 mmol) in THF (150 mL) at −78° C. was added n-butyl lithium (30 mL, 1.6 M solution in hexanes, 48.1 mmol) and the reaction stirred at this temperature for 30 minutes. Trimethylsilyl chloride (6.1 mL, 48.1 mmol) was then added and the solution stirred at −78° C. for 1.5 hours. The reaction was allowed to warm to room temperature and water (75 mL) was added. The mixture was extracted with diethyl ether (2×75 mL) and the combined organic extracts were dried (magnesium sulphate) and concentrated under reduced pressure to afford 2-methyl-5-(trimethylsilyl)phenoxytrimethylsilane (5 g) as a yellow oil. 1H NMR δH 0.26 (9 H, s), 0.29 (9 H, s), 2.20 (3 H, s), 6.93 (1 H, d, J=1.1 Hz), 7.04 (1 H, dd, J=7.3, 1.1 Hz), 7.16 (1 H, d, J=7.4 Hz).

Workup

  1. stirringthe solution stirred at −78° C. for 1.5 hours
  2. extractionThe mixture was extracted with diethyl ether (2×75 mL)
  3. dry with materialthe combined organic extracts were dried (magnesium sulphate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94d203fd3bfe4f7f9eceaaaf3f0fc14c
Source dataset
uspto-grants-2008_08
Patent number
US07407649B2

Reaction notes

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