Imidazole → (4-((5-Bromo-2-chlorothiophen-3-yl)methyl)phenoxy)(tert-butyl)dimethylsilane

HRID 1469185Notes

Reaction equation

HRID 1469185 reaction equation
[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1C=CN=C1>CN(C=O)C.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][Si:20]([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21])=[CH:11][CH:10]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 666909044-((5-Bromo-2-chlorothiophen-3-yl)methyl)phenol

Product 1

HCID 66693681(4-((5-Bromo-2-chlorothiophen-3-yl)methyl)phenoxy)(tert-butyl)dimethylsilaneYield 99.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of phenol 4 (3.0 g, 9.88 mmol) in DMF (20 mL) were added TBDMSCl (1M in CH2Cl2, 20 mL, 19.8 mmol), imidazole (2.1 g, 29.6 mmol) and DMAP (0.25 g, 1.98 mmol) at room temperature. The mixture was stirred at ambient temperature for 14 hours. The mixture was extracted with EtOAc/H2O (75 mL/250 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the title compound 21 (4.12 g, 99%).

Workup

  1. extractionThe mixture was extracted with EtOAc/H2O (75 mL/250 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-04fda64dab7940a19c49a76a03745de3
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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