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

HRID 1011490ノート

反応式

HRID 1011490 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 231171383-(Bromomethyl)-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazole収率 68%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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 3-(bromomethyl)-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazole (15.1 g, 68%).

後処理

  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)

出典と根拠

ORDレコード
ord-38e7fa6236b646718fdd6e7c03d8fed1
出典データセット
uspto-grants-2011_07
特許番号
US07977364B2

反応ノート

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