Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

HRID 1792416Notes

Reaction equation

HRID 1792416 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].CO>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 887MethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 108595834-Bromobenzyloxy-tert-butyldimethylsilaneYield 91%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of p-bromobenzyl alcohol (5.0 g, 26.7 mmol) in DMF (10 mL) was added imidazole (4.54 g, 66.7 mmol) followed by addition of tert-butyldimethylsilyl chloride (6.01 g, 40 mmol). The progress of the reaction was monitored by TLC. When the reaction was complete (about 2 h), methanol was added and diluted by 20% ethyl acetate in hexane. The organic layer was washed several times with water and then with brine, dried, concentrated under reduced pressure to give 7.5 g of the crude product which was passed through a short column chromatography to give 7.3 g (91%) of the desired compound.

Workup

  1. additionwas added
  2. washThe organic layer was washed several times with water
  3. dry with materialwith brine, dried
  4. concentrationconcentrated under reduced pressure
  5. customto give 7.5 g of the crude product which

Sources & evidence

ORD record
ord-7696eefa70854ec68278c2cac1e07693
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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