Triisopropylsilyl chloride → (5-Bromo-2-chlorobenzyloxy)triisopropylsilane

HRID 2042911Notes

Reaction equation

HRID 2042911 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7][OH:8].[CH:11]([Si:14](Cl)([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])([CH3:13])[CH3:12]>CN(C=O)C.CN(C)C1C=CN=CC=1.[Cl-].[NH4+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7][O:8][Si:14]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:11]([CH3:13])[CH3:12]

Participants

6

Reactant 2

HCID 139400Triisopropylsilyl chlorideHCID 5074766(5-Bromo-2-chlorophenyl)methanol

Product 1

HCID 67153939(5-Bromo-2-chlorobenzyloxy)triisopropylsilaneYield 95%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 5-bromo-2-chlorobenzyl alcohol (425 mmol) in DMF (400 mL) was added imidazle (58 g, 850 mmol), 4-(dimethylamino)pyridine (2.6 g, 21 mmol), and triisopropylsilyl chloride (136 mL, 638 mmol). The resulting solution was stirred at ambient temperature for 15 h, diluted with a saturated ammonium chloride and extracted with EtOAc. The organic layer was washed with water then brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to yield the titled compound 32 (152 g, 403 mmol, 95%) as a colorless oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-a8f79c370d624ad3a9e077eb6c9775a6
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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