Dimethylformamide → (4-Bromo-2,6-dichlorophenoxy)(tert-butyl)dimethylsilane

HRID 965969Notes

Reaction equation

HRID 965969 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.CN(C=O)C.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>O>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 185874-Bromo-2,6-dichlorophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 22313824(4-Bromo-2,6-dichlorophenoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-bromo-2,6-dichlorophenol (11.9 g, 49.2 mmol, H. Joyce et al., J. Amer. Chem. Soc., 39, 2644 (1917)) in DMF (100 mL) imidazole (5.0 g, 74 mmol) and tert-butyldimethylsilylchloride (8.9 g, 59 mmol) was added at room temperature and the mixture was stirred for 1 h. The mixture was poured into water (300 mL) and extracted with diethyl ether (100 mL×2) and washed with water (50 mL×2), dried over MgSO4 and concentrated in vacuo gave pale yellow oil. (15.3 g, 87%)

Workup

  1. extractionextracted with diethyl ether (100 mL×2)
  2. washwashed with water (50 mL×2)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customgave pale yellow oil

Sources & evidence

ORD record
ord-0d5728ed55df4606b2863ce06bd66af9
Source dataset
uspto-grants-2005_10
Patent number
US06951876B2

Reaction notes

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