Imidazole → HCID 90310712, compound

HRID 1519152Notes

Reaction equation

HRID 1519152 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].CN(C=O)C.N1C=CN=C1.[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 27792842-BROMO-6-FLUOROPHENOL

Product 1

HCID 90310712HCID 90310712, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A 500-mL three-neck, round bottomed flask, equipped with a stir bar, temperature probe and nitrogen inlet, was charged with 2-bromo-6-fluorophenol (25 g, 130.9 mmol, 1.00 eq), DMF (252 mL, 0.52 M), imidazole (12.3 g, 181 mmol, 1.38 eq) and tertbutyldimethylsilyl chloride (19.7 g, 131 mmol, 1.00 eq). The mixture was heated at 60° Celsius for 3 hours. The reaction was cooled to room temperature and diluted with water. The aqueous phase was extracted with ethyl acetate and the resultant organic solution washed with water and brine and dried over sodium sulfate. The organic phase was concentrated to dryness and purified using FCC to provide (2-bromo-6-fluorophenoxy)(tert-butyl)dimethylsilane as a colorless oil (33 g, 82%).

Workup

  1. customA 500-mL three-neck, round bottomed flask, equipped with a stir bar
  2. temperatureThe reaction was cooled to room temperature
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe resultant organic solution washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase was concentrated to dryness
  7. custompurified

Sources & evidence

ORD record
ord-738d8dc608c5445e877f1a6444803283
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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