Imidazole → HCID 58230556, compound

HRID 390395Notes

Reaction equation

HRID 390395 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[C:5]([O:11][CH3:12])[CH:4]=1.N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19]>ClCCl>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23])=[C:5]([O:11][CH3:12])[CH:4]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67087115HCID 67087115, compound

Product 1

HCID 58230556HCID 58230556, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromomethyl-2-methoxy-phenyl)-methanol (1.1 g, 4.76 mmol) in dichloromethane (15 mL) is added imidazole (0.861 g, 5.71 mmol) and tert-butylchlorodimethylsilane (0.971 g, 12.98 mmol) at 0° C. The reaction mixture is allowed to warm to room temperature and stirred for one hour. The reaction mixture is quenched with water and concentrated. The residue is diluted with DCM, washed with water (15 mL) and brine (15 mL), dried over sodium sulfate, filtered, and concentrated to give the title compound (1.1 g, 66.9%). 1H NMR (400 MHz, CDCl3) δ 7.43-7.41 (d, J=8 Hz, 1H), 7.00-6.98 (d, J=8 Hz, 1H), 6.94 (s, 1H), 4.73 (s, 2H), 4.50 (s, 2H), 3.83 (s, 3H), 0.95 (s, 9H), 0.10 (s, 6H).

Workup

  1. customThe reaction mixture is quenched with water
  2. concentrationconcentrated
  3. additionThe residue is diluted with DCM
  4. washwashed with water (15 mL) and brine (15 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6651193da1934c9bb06446d6d063dc68
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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