tert-Butyldimethylsilyl chloride → 2-(t-Butyldimethylsilyl)-3-bromo-4-methoxy benzaldehyde

HRID 131092Notes

Reaction equation

HRID 131092 reaction equation
O[C:2]1[C:9]([Br:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CN(C=O)C>[Si:13]([C:2]1[C:9]([Br:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 141209453-Bromo-2-hydroxy-4-methoxybenzaldehyde

Product 1

HCID 223492562-(t-Butyldimethylsilyl)-3-bromo-4-methoxy benzaldehydeYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diiospropylethylamine (3.0 ml) was added to a stirred solution (under argon) of 2-hydroxy-3-bromo- -4-methoxybenzaldehyde (1.96, 8.5 mmole) in DMF (15 ml) followed by t-butyldimethlsilyl chloride (TBSCl, 1.91 g, 12.8 mmole). The reaction mixture was stirred at room temperature for 30 min and Ice (20 g) was added to the mixture. The mixture was then extracted with ether (3×25 ml). The ethereal solution was washed with water (25 ml) and saturated NaHCO3 solution (2×15 ml). The solvent evaporated to yield 2-(t-butyldimethylsilyl)-3-bromo-4-methoxy benzaldehyde as an oil (2.54 g, 7.06 mmole, 83.1%).

Workup

  1. extractionThe mixture was then extracted with ether (3×25 ml)
  2. washThe ethereal solution was washed with water (25 ml) and saturated NaHCO3 solution (2×15 ml)
  3. customThe solvent evaporated

Sources & evidence

ORD record
ord-705325ef04a849a39f8f6379eeb183ef
Source dataset
uspto-grants-2008_06
Patent number
US07384925B2

Reaction notes

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