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

HRID 1242094Notes

Reaction equation

HRID 1242094 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.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>ClC(Cl)(Cl)Cl>[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 3

HCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 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 1

HCID 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, 13 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-13122a0b7af2436393312ec0f0eaeeef
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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