1,3,5-Tri-tert-butylbenzene → 1-Bromo-3,5-di-tert-butylbenzene

HRID 1017154

反応式

HRID 1017154 の反応式
[C:1]([C:5]1[CH:10]=[C:9](C(C)(C)C)[CH:8]=[C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:19]Br>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[C:9]([Br:19])[CH:8]=[C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 150891,3,5-Tri-tert-butylbenzeneHCID 24408Bromine

生成物 1

HCID 6201361-Bromo-3,5-di-tert-butylbenzene収率 61.9%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒2 回

反応条件

温度
0 °C

実験手順

1,3,5-Tri-t-butylbenzene (150 g, 0.6 mol) was dissolved in 600 mL of carbon tetrachloride in a three-neck flask painted black to avoid light; The flask was equipped with an overhead stirrer, a thermometer, and an addition funnel under argon. Ferric chloride (3.0 g, 0.018 mol) was added and the solution was cooled to 0° C. A solution of bromine (120 g, 0.75 mol) dissolved in 200 mL of carbon tetrachloride was then added over a 2-hour period. The solution was stirred for an additional 1 hour at 0° C. and quenched with ice water. The layers were separated and the organics washed with 10% sodium hydroxide solution. The solution was then washed with salt brine and dried over magnesium sulfate. The solvent was removed under vacuum and the product was distilled through a 2-ft (60-cm) column under vacuum two times. The fractions boiling at 90°-110° C. at 0.4 mm Hg were combined and recrystallized from heptane to give 100 g of pure 3,5-di-t-butylbromobenzene (60% yield).

後処理

  1. customThe flask was equipped with an overhead stirrer
  2. additionwas then added over a 2-hour period
  3. customquenched with ice water
  4. customThe layers were separated
  5. washthe organics washed with 10% sodium hydroxide solution
  6. washThe solution was then washed with salt brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under vacuum
  9. distillationthe product was distilled through a 2-ft (60-cm) column under vacuum two times
  10. customrecrystallized from heptane

出典と根拠

ORDレコード
ord-3a6222c2aa8d451d9cb45bff096f2da1
出典データセット
uspto-grants-2002_11
特許番号
US06479424B1

関連ノート

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