Imidazole → HCID 58968658, compound

HRID 2075074Notes

Reaction equation

HRID 2075074 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12][OH:13].N1C=CN=C1.[CH:19]([Si:22](Cl)([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])([CH3:21])[CH3:20]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=1[CH2:12][O:13][Si:22]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:19]([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 27562482-Bromo-5-(trifluoromethyl)benzyl alcohol

Product 1

HCID 58968658HCID 58968658, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-bromo-5-(trifluoromethyl)phenyl)methanol (10 g; 39 mmol) in N,N-dimethylformamide (100 mL) was added imidazole (6.82 g; 100.1 mmol) and triisopropylsilyl chloride (9.6 mL; 55.2 mmol) under N2. The reaction was stirred at room temperature for 48 hours. The reaction was diluted with ethyl acetate and washed with water (4×) and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by 80 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-10% ethyl acetate in heptane) to yield the title compound (16.47 g, 100%) as a colorless oil. MS (GC) Calc: 410.0, Found: 391 (M−F). 1H NMR (400 MHz, CDCl3) δ ppm 7.94 (s, 1H), 7.62 (d, J=8.30 Hz, 1H), 7.39 (d, J=8.30 Hz, 1H), 4.84 (s, 2H), 1.25 (m, 3H), 1.12(d, 18H).

Workup

  1. washwashed with water (4×) and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by 80 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-7a1bd7b475dc4d9a814889cb1d322317
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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