tert-Butyldimethylsilyl chloride → (4-Bromo-2,6-dimethylphenethoxy)(tert-butyl)dimethylsilane

HRID 735624Notes

Reaction equation

HRID 735624 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[C:4]([CH2:18]C)[CH:3]=1.Br[C:21]1C=C(C)C(CCO)=C(C)C=1.C([Si](Cl)(C)C)(C)(C)C>>[Br:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11])=[C:16]([CH3:21])[CH:17]=1

Participants

4

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 57842587(4-Bromo-2-ethylphenethoxy)(tert-butyl)dimethylsilaneHCID 578427022-(4-Bromo-2,6-dimethylphenyl)ethanol

Product 1

HCID 57842569(4-Bromo-2,6-dimethylphenethoxy)(tert-butyl)dimethylsilaneYield 80%

Procedure

Using a procedure analogous to that used to prepare 46A, 32B (3.0 g, 13.1 mmol) was reacted tert-butylchlorodimethylsilane to afford 50A (3.58 g, 80%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm −0.01 (s, 9 H) 2.30 (s, 6 H) 2.84 (t, J=7.70 Hz, 2 H) 3.66 (t, J=7.70 Hz, 2 H) 7.13 (s, 2 H).

Sources & evidence

ORD record
ord-c9e70ac44d1c47ad93096ec1414efd30
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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