Imidazole → ((2-Bromo-5-methoxybenzyl)oxy)(tert-butyl)dimethylsilane

HRID 392875Notes

Reaction equation

HRID 392875 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4][OH:5].N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].CCOCC>C1COCC1.O.CCCCCC>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4][O:5][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl Ether2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 10867706(2-Bromo-5-methoxyphenyl)methanol

Product 1

HCID 22662093((2-Bromo-5-methoxybenzyl)oxy)(tert-butyl)dimethylsilaneYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under a nitrogen atmosphere, 23.0 g (0.11 mol) of 2-bromo-5-methoxybenzyl alcohol (13) was dissolved in 100 mL of anhydrous THF. 14.43 g (0.21 mol) of imidazole was added, followed by 17.6 g (0.12 mol) of t-butyl dimethylsilylchloride. The reaction mixture was allowed to stir overnight at ambient temperature. Ether was added and the reaction was diluted with water (200 mL). The aqueous layer was separated and extracted with ether (2×300 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford crude product. The crude product was loaded onto a 4 inch×6 inch silica gel column. Using 40% ether in hexane as an eluant afforded 33.63 g (96%) of (2-bromo-5-methoxy-benzyloxy)-tert-butyl-dimethyl-silane (14).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ether (2×300 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford crude product

Sources & evidence

ORD record
ord-0ddb252bab5749239ea6e932cd44cdca
Source dataset
uspto-grants-2004_10
Patent number
US06803470B2

Reaction notes

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