Imidazole → HCID 18971711, compound

HRID 2395383Notes

Reaction equation

HRID 2395383 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1.[OH2:22]>CN(C=O)C>[Si:9]([O:8][C:3]1[C:2]([F:1])=[C:7]([OH:22])[CH:6]=[CH:5][CH:4]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 97072-FluorophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 18971711HCID 18971711, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-fluorophenol (10.35 g, 9.2 mmol) and tert-butyldimethylsilyl chloride (101 mmol) in DMF (180 ml) was added imidazole (7.54 g, 110 mmol) in one portion. After stirring for 3 h the reaction mixture was poured into water (300 ml) and extracted with diethyl ether (3×100 ml). The combined extracts were washed with 10% aqueous citric acid (100 ml), brine (100 ml), dried (MgSO4) and concentrated under reduced pressure to afford title compound (20.63 g, quant.) as a colorless liquid.

Workup

  1. extractionextracted with diethyl ether (3×100 ml)
  2. washThe combined extracts were washed with 10% aqueous citric acid (100 ml), brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b04002c825b4ab6a8c25e5579aa2be3
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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