Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

HRID 1080720Notes

Reaction equation

HRID 1080720 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C(Cl)Cl>[O:7]([CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 3

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

Product 1

HCID 108595834-Bromobenzyloxy-tert-butyldimethylsilaneYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 26.28 g (0.141 mol) of 4-bromobenzyl alcohol and 19.1 g (0.28 mol) of imidazole in 100 mL of methylene chloride was treated dropwise with a solution of 21.18 g (0.14 mol) of t-butyldimethylsilyl chloride in 50 mL of methylene chloride. The reaction mixture was stirred at room temperature for 30 minutes then transferred to a separatory funnel and washed with water, 1N hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The organic layer was removed, dried over magnesium sulfate, filtered and solvents removed under vacuum giving 41 g of the product as a colorless, viscous oil. 1H NMR (200 MHz, CDCl3): 0.09 (s, 6H), 0.93 (s, 9H), 4.67 (s, 2H), 7.18 (d, 8 Hz, 2H), 7.43 (d, 8 Hz, 2H).

Workup

  1. customthen transferred to a separatory funnel
  2. washwashed with water, 1N hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  3. customThe organic layer was removed
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-cc18588edb2543f48240fb4a346dc44a
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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