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

HRID 896393Notes

Reaction equation

HRID 896393 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 chloride2×HCID 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-8b1f9152f85d43c3a1c8991164d2c42d
Source dataset
uspto-grants-2005_07
Patent number
US06919324B2

Reaction notes

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