N-bromobutanimide → 3-(Bromomethyl)-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazole

HRID 1921272Notes

Reaction equation

HRID 1921272 reaction equation
C1C(=O)N([Br:8])C(=O)C1.C(OOCC1C=CC=CC=1)C1C=CC=CC=1.[CH3:25][C:26]1[C:30]2[CH:31]=[CH:32][C:33]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])=[CH:34][C:29]=2[O:28][N:27]=1>C(Cl)(Cl)(Cl)Cl>[Br:8][CH2:25][C:26]1[C:30]2[CH:31]=[CH:32][C:33]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])=[CH:34][C:29]=2[O:28][N:27]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 11229634Benzyl PeroxideHCID 231171073-Methyl-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazole

Product 1

HCID 231171383-(Bromomethyl)-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

NBS (12.7 g, 71.5 mmoles) and benzyl peroxide (1.6 g, 6.5 mmoles) were added to a mixture of 3-methyl-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazole (17.1 g, 65 mmoles) and CCl4 (200 ml). The mixture was refluxed overnight and the precipitate was filtered, washed with CCl4 and purified by flash chromatography (AcOEt/Toluene 1/9 with 0.1% TEA) to give

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationthe precipitate was filtered
  3. washwashed with CCl4
  4. custompurified by flash chromatography (AcOEt/Toluene 1/9 with 0.1% TEA)
  5. customto give

Sources & evidence

ORD record
ord-99b9130766cd46d085ab04dbbd2784fd
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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