Isoamyl Nitrite → (4-Bromo-5-fluoro-2-methylphenyl)(methyl)sulfane

HRID 407868ノート

反応式

HRID 407868 の反応式
[Br:1][C:2]1[C:8]([F:9])=[CH:7][C:5](N)=[C:4]([CH3:10])[CH:3]=1.[CH3:11][S:12]SC.N(OCCC(C)C)=O>>[Br:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([S:12][CH3:11])=[C:4]([CH3:10])[CH:3]=1

参加物

4

反応物 3

HCID 8053Isoamyl NitriteHCID 12232Dimethyl DisulfideHCID 70180444-Bromo-5-fluoro-2-methylaniline

生成物 1

HCID 67469729(4-Bromo-5-fluoro-2-methylphenyl)(methyl)sulfane収率 85%

反応条件

温度
75 °C

実験手順

4-Bromo-5-fluoro-2-methylaniline (5 g, 24.5 mmol) was dissolved in 1,2-dimethyldisulfane (35 mL, 394 mmol) and heated to 75° C. under nitrogen. Isoamyl nitrite (8.52 mL, 63.7 mmol) was added dropwise to the reaction via an addition funnel through a reflux condenser (˜1 drop/sec). (NOTE—a large exotherm may occur if addition is too fast.) After addition was complete, the reaction was heated to 95° C. for 1 hour and allowed to cool to ambient temperature. The reaction was concentrated and purified over silica gel (100% hexanes) to afford (4-bromo-5-fluoro-2-methylphenyl)(methyl)sulfane (4.9 g, 20.8 mmol, 85.0% yield) as an orange solid.

後処理

  1. addition(NOTE—a large exotherm may occur if addition
  2. addition) After addition
  3. temperaturethe reaction was heated to 95° C. for 1 hour
  4. temperatureto cool to ambient temperature
  5. concentrationThe reaction was concentrated
  6. custompurified over silica gel (100% hexanes)

出典と根拠

ORDレコード
ord-329663c429d0481c9a242f90f4f893ee
出典データセット
uspto-grants-2014_06
特許番号
US08754226B2

反応ノート

読み込み中…