Imidazole → ((4-Bromo-2-methoxybenzyl)oxy)(tert-butyl)dimethylsilane

HRID 1888459Notes

Reaction equation

HRID 1888459 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[C:12]([O:18][CH3:19])[CH:11]=1.N1C=CN=C1>CN(C=O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 151282434-Bromo-2-methoxybenzyl alcohol

Product 1

HCID 18687376((4-Bromo-2-methoxybenzyl)oxy)(tert-butyl)dimethylsilaneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethylsilyl chloride (1.04 g, 6.9 mmol) was added to a mixture of (4-bromo-2-methoxyphenyl)methanol (1.0 g, 4.6 mol) and imidazole (470 mg, 7.0 mmol) in DMF (15 mL) and the resultant mixture was stirred at ambient temperature for 66 h. The mixture was concentrated to about a third of the original volume then diluted with water and extracted with diethyl ether (×3). The combined organic layer was dried over magnesium sulfate, filtered and evaporated. The resultant residue was purified by chromatography (silica, 50 g column, Si-SPE, 5% diethyl ether in pentane) to afford the title compound as a colourless oil (1.51 g, 98%). 1H NMR (CDCl3, 400 MHz): 7.34 (dt, J=8.1, 1.05 Hz, 1H); 7.11 (dd, J=8.1, 1.8 Hz, 1H); 6.95 (d, J=1.8 Hz, 1H); 4.69 (d, J=1.0 Hz, 2H); 3.81 (s, 3H); 0.97-0.94 (m, 9H); 0.13-0.08 (m, 6H).

Workup

  1. concentrationThe mixture was concentrated to about a third of the original volume
  2. additionthen diluted with water
  3. extractionextracted with diethyl ether (×3)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant residue was purified by chromatography (silica, 50 g column, Si-SPE, 5% diethyl ether in pentane)

Sources & evidence

ORD record
ord-314efdb7205a43e98f10d5efb3d51ab3
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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