tert-Butyldimethylsilyl chloride → (4-Bromo-3-methoxyphenoxy)(tert-butyl)dimethylsilane

HRID 579308Notes

Reaction equation

HRID 579308 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].CCN(C(C)C)C(C)C.[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21]>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 57422590(4-Bromo-3-methoxyphenoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Bromo-3-methoxyphenol (254 g, 1251 mmol) was dissolved in DCM (2500 mL) and treated with DIPEA (437 mL, 2502 mmol) under nitrogen atmosphere. tert-Butylchlorodimethylsilane (198 g, 1314 mmol) was added and the reaction mixture was stirred at room temperature overnight. The crude product was diluted with water and the organic layer was extracted then dried over sodium sulfate and concentrated.

Workup

  1. extractionthe organic layer was extracted
  2. dry with materialthen dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a2b455ecab724fa0acea2f1c3f70aabc
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

Loading…