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

HRID 1746024Notes

Reaction equation

HRID 1746024 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-9f1da921f36d4e47a7d9e2469f6690fd
Source dataset
uspto-grants-2015_10
Patent number
USRE045720E1

Reaction notes

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