Imidazole → 1-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene

HRID 2268698Notes

Reaction equation

HRID 2268698 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](CO)=[CH:4][CH:3]=1.N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].CN([CH:26]=[O:27])C>O>[Br:1][C:2]1[CH:9]=[CH:8][CH:5]=[C:4]([CH2:26][O:27][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzeneYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1-L round-bottomed flask were added 4-bromobenzyl alcohol (100.0 g, 0.53 mol), imidazole (91.0 g, 1.34 mol), t-butyldimethylsilyl chloride (TBDMS-Cl) (96.5 g, 0.64 mol), and DMF 100 mL. The reaction mixture was stirred at room temperature under nitrogen overnight. The reaction was poured into water and extracted with ether three times and the combined organic phase was washed with water three times and dried over MgSO4. After solvent was removed, the product was obtained as light yellow liquid 154 g (62% yield). 1H NMR (CDCl3) δ (Ppm): 0.07 (s, 9H), 0.91 (s, 6H), 4.65 (s, 2H), 7.17 (d, J=8.2 Hz, 2H), 7.42 (s, J=8.3 Hz, 2H); 13C NMR (CDCl3): −1.71, 21.93, 29.48, 67.89, 124.13, 131.27, 134.82, 144.02; FD-MS: m/z 301 (M+).

Workup

  1. extractionextracted with ether three times
  2. washthe combined organic phase was washed with water three times
  3. dry with materialdried over MgSO4
  4. customAfter solvent was removed

Sources & evidence

ORD record
ord-669ac669188d4563b370a59a1b02b998
Source dataset
uspto-grants-2001_12
Patent number
US06329086B1

Reaction notes

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