Dichloromethane → (4-Bromo-3-methoxyphenoxy)(tert-butyl)dimethylsilane

HRID 1027224Notes

Reaction equation

HRID 1027224 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].C(Cl)Cl.CCN(C(C)C)C(C)C.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 57422590(4-Bromo-3-methoxyphenoxy)(tert-butyl)dimethylsilaneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 5 L round bottom flask fitted with an overhead stirrer, thermocouple and N2 inlet, was added 4-bromo-3-methoxyphenol (254 g, 1251 mmol), DCM (2500 mL) and DIPEA (437 mL, 2502 mmol). The reaction mixture was cooled in an ice bath, followed by addition of tert-butylchlorodimethylsilane (198 g, 1314 mmol). The reaction mixture was stirred at RT overnight, and then diluted with water. The organic layer was separated, dried over sodium sulfate, filtered and concentrated to provide (4-bromo-3-methoxyphenoxy)(tert-butyl)dimethylsilane (472 g, 1250 mmol, 100% yield). MS (M+1)=319.2.

Workup

  1. customTo a 5 L round bottom flask fitted with an overhead stirrer
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a5dc3b954b20420a99c5c9a9de1a604c
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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