N-bromobutanimide → (3-(Bromomethyl)phenyl)trimethylsilane

HRID 1265953Notes

Reaction equation

HRID 1265953 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1.C1C(=O)N([Br:19])C(=O)C1>CC(N=NC(C#N)(C)C)(C#N)C.ClC1C=CC=CC=1>[CH3:1][Si:2]([CH3:10])([CH3:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH2:9][Br:19]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10866684Trimethyl(M-tolyl)silane

Product 1

HCID 12583977(3-(Bromomethyl)phenyl)trimethylsilaneYield 99.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of m-trimethylsilyltoluene (8.22 g, 50 mmol), NBS (8.90 g, 50 mmol), AIBN (0.05 g) and chlorobenzene (50 ml) was heated by means of a heating bath preheated to 110° C. An exothermic reaction started when the reaction mixture reached 80-90° C. and the orange suspension became a colorless solution within minutes. The mixture was cooled down with the aid of an ice-bath, ice water was added and the resulting mixture was extracted with hexane. The organic phase was washed with water, then brine and dried (MgSO4). Filtration through a silica plug (10 g) followed by evaporation of solvents yielded 12.05 g (99%) of 37 as a colorless liquid. Spectroscopic data were identical to those reported in the literature.43

Workup

  1. temperaturewas heated by means of a heating bath
  2. custompreheated to 110° C
  3. customAn exothermic reaction
  4. customreached 80-90° C.
  5. temperatureThe mixture was cooled down with the aid of an ice-bath
  6. extractionthe resulting mixture was extracted with hexane
  7. washThe organic phase was washed with water
  8. dry with materialbrine and dried (MgSO4)
  9. filtrationFiltration through a silica plug (10 g)
  10. customfollowed by evaporation of solvents

Sources & evidence

ORD record
ord-b9a1c361dc1743b78a88c1f5d3b418a9
Source dataset
uspto-grants-2003_04
Patent number
US06548042B2

Reaction notes

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