tert-Butyldimethylsilyl chloride → {[4-(Bromomethyl)phenyl]methoxy}(tert-butyl)dimethylsilane

HRID 2255569Notes

Reaction equation

HRID 2255569 reaction equation
[Br:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:8][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 103304344-(Bromomethyl)benzyl alcohol

Product 1

HCID 10757711{[4-(Bromomethyl)phenyl]methoxy}(tert-butyl)dimethylsilaneYield 71%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step A (4.44 g, 22.1 mmol) in CH2Cl2 were added N,N-diisopropylethylamine (1.2 eq.), 4-dimethylaminopyridine (0.1 eq), and tert-butyldimethylsilyl chloride (1.2 eq). The reaction mixture was stirred for 1.5 hours at room temperature, then concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water, brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluted with 2.5% ethyl acetate/hexane to afford 5.0 g (71%) of the titled product.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluted with 2.5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f462da1e6ab14abeb17108676af51d46
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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