N-bromobutanimide → [3-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane

HRID 1710881ノート

反応式

HRID 1710881 の反応式
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH2:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:15])[CH3:14]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 529234tert-Butyl(dimethyl)(3-methylphenoxy)silane

生成物 1

HCID 10040514[3-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane収率 62%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a solution of tert-butyldimethyl(m-tolyloxy)silane (1.31 g, 5.9 mmol) in CCl4 (30 mL) was added N-bromosuccinimide (1.13 g, 6.5 mmol), followed by benzoyl peroxide (55 mg, 0.2 mmol). The reaction was refluxed for 1 h, then cooled to room temperature. It was filtered and filtrate was concentrated and purified by column chromatography on ISCO with 10% ethyl acetate in hexanes to yield (3-(bromomethyl)phenoxy)(tert-butyl)dimethylsilane as a colorless oil (1.1 g, 62%). HPLC retention time (Method C)=4.44 min. LC/MS (ESI) (M+H)+=301.

後処理

  1. temperatureThe reaction was refluxed for 1 h
  2. filtrationIt was filtered
  3. concentrationfiltrate was concentrated
  4. custompurified by column chromatography on ISCO with 10% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-3dddbd2ea4b74d5eab1b6066125f6f88
出典データセット
uspto-grants-2010_09
特許番号
US07790745B2

反応ノート

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