N-bromobutanimide → 6-Bromomethyl-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid ethyl ester

HRID 2188015Notes

Reaction equation

HRID 2188015 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:2].[Br:21]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:10]([CH2:11][Br:21])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 69585527Ethyl 2-((tert-butyldimethylsilyl)oxy)-6-methylbenzoate

Product 1

HCID 695855186-Bromomethyl-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid ethyl esterYield 83.1%

Reagents, catalysts & solvents 2

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)CatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-benzoic acid ethyl ester (7.6 g, 25.8 mmol), N-bromosuccinimide (4.82 g, 27.1 mmol) and azobis(cyclohexanecarbonitrile) (0.32 g, 1.3 mmol) were dissolved in tetrachlormethane (130 ml). The solution was stirred at room temperature for 60 hours. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel column using a gradient of 1-2% ethyl acetate/hexane as eluent, which afforded 8.0 g (83%) of 6-bromomethyl-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid ethyl ester as an oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-40cd6be5a9694487a57f2b1ffa13d5d7
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

Loading…