1,1-Dichloroethane → (4-Bromo-3-bromomethyl-phenoxy)-tert-butyl-dimethyl-silane

HRID 1181049Notes

Reaction equation

HRID 1181049 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[CH:4][C:3]=1[CH3:16].ClC(Cl)C.[Br:21]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:8])[CH3:9])=[CH:4][C:3]=1[CH2:16][Br:21]

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 17984598(4-Bromo-3-methylphenoxy)(tert-butyl)dimethylsilane

Product 1

HCID 19437125(4-Bromo-3-bromomethyl-phenoxy)-tert-butyl-dimethyl-silane

Conditions

Temperature
47 °C

Procedure

(4-Bromo-3-methyl-phenoxy)-tert-butyl-dimethyl-silane (255 g, 0.846 mol), dichloroethane (2.5 L), N-bromosuccinimide (165 g, 0.927 mol) and 2,2′-azobisisobutyronitrile (19.0 g, 0.116 mol) were combined in a 5 L flask. The mixture was degassed by evacuating and purging with N2 (5×). The reaction mixture was heated to 47° C., and the heat was shut off. An exotherm to 76° C. occurred. GC analysis showed 6.5% unreacted starting material. The heat was applied again, and the reaction was held at reflux (83° C.) for 15 min. After cooling to 8° C., heptane (1.0 L) was added. The resulting slurry was stirred at 4° C. for 30 min and filtered. The filtrate was evaporated to dryness. The residue was treated with heptane (1 L), placed in the freezer overnight, and filtered. The filtrate was concentrated to the title compound (326 g, 101%).

Workup

  1. customThe mixture was degassed
  2. customby evacuating
  3. custompurging with N2 (5×)
  4. customto 76° C.
  5. temperatureat reflux (83° C.) for 15 min
  6. temperatureAfter cooling to 8° C.
  7. additionheptane (1.0 L) was added
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. additionThe residue was treated with heptane (1 L)
  11. customplaced in the freezer overnight
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated to the title compound (326 g, 101%)

Sources & evidence

ORD record
ord-1144e65b9607487ba2b66c45a236f9d5
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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