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

HRID 2399460Notes

Reaction equation

HRID 2399460 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 sq.), 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-7b92fd03aed442aaa6a794fb6f1ddb90
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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