N-bromobutanimide → HCID 59776518, compound

HRID 1438411Notes

Reaction equation

HRID 1438411 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].[Br:18]N1C(=O)CCC1=O.O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:18][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:4]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 12007214HCID 12007214, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 59776518HCID 59776518, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (50 ml) solution of 1-Amino-2-[2-(tert-butyldimethylsilyloxy)ethyl]benzene (3.96 g, 0.015 mol) [European journal of organic chemistry, 2001, issue 48, 2447-2462] was added N-bromosuccinimide (2.67 g, 0.015 mol) and the mixture was stirred at ambient temperature for 24 hours. Then, the reaction was poured onto saturated aqueous sodium bicarbonate water and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtration and evaporation. The crude material was purified through silica gel column chromatography eluting with hexane/ethyl acetate (10:1 to 5:1) to afford 3.62 g (73% yield) of the title compound as brown oil.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate, filtration and evaporation
  3. customThe crude material was purified through silica gel column chromatography
  4. washeluting with hexane/ethyl acetate (10:1 to 5:1)

Sources & evidence

ORD record
ord-cc33c94a9fc543e0bdcd72989e7fbc02
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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