Triethylamine → (4-Bromo-3,5-dimethylphenoxy)(tert-butyl)dimethylsilane

HRID 237498Notes

Reaction equation

HRID 237498 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].C(N(CC)CC)C.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19]>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 16128203(4-Bromo-3,5-dimethylphenoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-Bromo-3,5-dimethylphenol (3.5 g), 4-(dimethylamino)pyridine (212 mg) and triethylamine (2.7 mL) are stirred in dichloromethane (25 mL) at 0° C., then tert-butyldimethylchlorosilane (19 mL) is added dropwise. The reaction mixture is warmed to ambient temperature and stirred overnight. The reaction mixture is diluted with dichloromethane, washed with aqueous HCl (1 M, 25 mL) and then with saturated aqueous NaHCO3 (25 mL). The organic phase is dried (MgSO4) and concentrated to give the title compound. Yield: 5.4 g

Workup

  1. washwashed with aqueous HCl (1 M, 25 mL)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a8b2774b682d4ac593a1ec4142bf9128
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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