N-bromobutanimide → (5-(Bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane

HRID 1801601ノート

反応式

HRID 1801601 の反応式
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[Cl:16])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:15][C:13]1[CH:12]=[CH:11][C:10]([Cl:16])=[C:9]([CH:14]=1)[O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 59803183Tert-butyl(2-chloro-5-methylphenoxy)dimethylsilane

生成物 1

HCID 59803153(5-(Bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane収率 34%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 6212Chloroform溶媒

反応条件

温度
85 °C

実験手順

A solution containing tert-butyl(2-chloro-5-methylphenoxy)dimethylsilane 80 (6.15 g, 24 mmol), N-bromosuccinimide (4.7 g, 26 mmol), and benzoyl peroxide (0.058 g, 0.24 mmol) in 40 mL of dry CHCl3 was purged with N2 and heated to 85° C. The reaction was exposed to a 60 W lamp and was stirred at reflux for 4 h. The lamp was removed and the reaction was cooled to room temperature. The solution was concentrated and was redissolved in ether. The mixture was filtered and then concentrated again. The crude material was purified by silica gel chromatography using a 5% to 20% gradient of EtOAc in hexanes as the eluant. The desired fractions were combined and concentrated to give (5-(bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane 81 (2.7 g, 34% yield). The product was carried forth to the next step as is.

後処理

  1. customwas purged with N2
  2. temperatureat reflux for 4 h
  3. customThe lamp was removed
  4. temperaturethe reaction was cooled to room temperature
  5. concentrationThe solution was concentrated
  6. dissolutionwas redissolved in ether
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated again
  9. customThe crude material was purified by silica gel chromatography
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-660a01eeb39c4108b2878d66517f8590
出典データセット
uspto-grants-2013_01
特許番号
US08349831B2

反応ノート

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