Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

HRID 1425704Notes

Reaction equation

HRID 1425704 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 108595834-Bromobenzyloxy-tert-butyldimethylsilaneYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromobenzyl alcohol (50.00 g, 267.3 mmol), tert-butyldimethylsilyl chloride (52.38 g, 347.5 mmol), and imidazole (23.66 g, 347.5 mmol) were dissolved in anhydrous DMF (300 mL). This solution was allowed to stir at room temperature overnight and then poured into ice-water (600 mL). The organic layer was separated off and washed with saturated aqueous sodium bicarbonate (2×200 mL) and water (2×200 mL). We obtained colorless oil (71.9 g, 88%): 1H NMR (CDCl3): δ 0.10 (s, (CH3)2Si), 0.94 (s, (CH3)3C), 4.7 (s, CH2O), 7.20 (d, J=7.8 Hz, C6H4), 7.45 (d, J=7.8 Hz, C6H4); 13C NMR (CDCl3): δ.

Workup

  1. customThe organic layer was separated off
  2. washwashed with saturated aqueous sodium bicarbonate (2×200 mL) and water (2×200 mL)

Sources & evidence

ORD record
ord-0cff806aa3fd4685ad8a795cca5697ff
Source dataset
uspto-grants-2015_01
Patent number
US08933065B2

Reaction notes

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