3,5-Dichlorophenol → Tert-butyl(3,5-dichlorophenoxy)dimethylsilane

HRID 1698852Notes

Reaction equation

HRID 1698852 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 115713,5-DichlorophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 18007485Tert-butyl(3,5-dichlorophenoxy)dimethylsilane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of CH2Cl6 (60 mL) and 3,5-dichlorophenol (5.0 g 30 mmol) was added tert-butyldimethylsilyl chloride (5.54 g, 36 mmol), N,N-diisoprpylethylamine (8.0 mL, 46 mmol) and a catalytic amount of 4-dimethylaminopyridine. The initially exothermic solution was stirred at ambient temperature for 6 h then diluted with CH2Cl2 (40 mL). The mixture was washed consecutively with 10% aqueous HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL). the organic phase was dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide 13 as a pale yellow liquied (8.8 g, 100%). 1H NMR (300 MHz, CDCl3) d 6.98 s, 1H), 6.72 (s, 2H), 0.98 (s, 9H), 0.22 (s, 6H).

Workup

  1. washThe mixture was washed consecutively with 10% aqueous HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
  2. dry with materialthe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84a3d863880240ee8e9e6db7e7287ffe
Source dataset
uspto-grants-2002_02
Patent number
US06344466B2

Reaction notes

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