Imidazole → tert-Butyl(2-fluorophenoxy)dimethylsilane

HRID 1662550

Reaction equation

HRID 1662550 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16].N1C=CN=C1>CN(C=O)C>[C:1]([Si:5]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[F:9])([CH3:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 97072-FluorophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 597214tert-Butyl(2-fluorophenoxy)dimethylsilaneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A 500 mL round bottom flask was charged with tert-butyldimethylchlorosilane (73.9 g, 491 mmol) (available from Aldrich), DMF (220 mL), 2-fluorophenol (41.3 mL, 446 mmol) (available from Aldrich), and imidazole (75.9 g, 1115 mmol). The pale yellow solution was stirred for 1.5 hours at 25° C. and diluted with hexanes (1 L). The organic phase was washed with water (1×300 mL), saturated aqueous NaHCO3 (3×300 mL), water (3×300 mL) and brine (1×300 mL). The organic phase was then dried (MgSO4), and concentrated to afford 84.A (101 g, 100% yield) as a colorless liquid. The crude product was used without further purification.

Workup

  1. washThe organic phase was washed with water (1×300 mL), saturated aqueous NaHCO3 (3×300 mL), water (3×300 mL) and brine (1×300 mL)
  2. dry with materialThe organic phase was then dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5b6227606bb5430e892a9cf79db46e80
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Linked notes

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