Imidazole → HCID 57443346, compound

HRID 2261834Notes

Reaction equation

HRID 2261834 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH:12]([Si:15](Cl)([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13].N1C=CN=C1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[O:11][Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 57443346HCID 57443346, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-fluoro-4-nitro-phenol (4.94 g, 31.4 mmol), triisopropylsilyl chloride (6.40 mL, 29.9 mmol), and imidazole (4.85 g, 70.7 mmol) in 70 mL of dichloromethane is stirred for 1.5 hours. Dichloromethane (100 mL) is added and the mixture is washed with water and brine, dried (MgSO4), and concentrated under reduced pressure. The residue is purified on silica gel (120 g) eluting with a gradient of ethyl acetate in heptane (0 to 80%) to provide the title compound (8.55 g, 87%) as an oil. ES/MS m/e 314.3.0 (M+1).

Workup

  1. washthe mixture is washed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified on silica gel (120 g)
  5. washeluting with a gradient of ethyl acetate in heptane (0 to 80%)

Sources & evidence

ORD record
ord-ef6847f799bd41fa83724b4fbafe4a16
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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