2-Bromobenzyl bromide → 2-(But-3-en-1-yl)bromobenzene

HRID 1836689ノート

反応式

HRID 1836689 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[CH2:10]([Mg]Br)[CH:11]=[CH2:12]>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][CH2:12][CH:11]=[CH2:10]

参加物

4

反応物 2

HCID 769652-Bromobenzyl bromideHCID 178455850HCID 178455850、化合物

生成物 1

HCID 34857122-(But-3-en-1-yl)bromobenzene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To an ice cold solution of 2-bromobenzyl bromide (5.00 g, 0.020 mol) in THF (25 mL) was added 1M allyl magnesium bromide (100 mL, 0.100 mol) slowly via cannula. The reaction mixture was stirred at reflux for 1.5 h, cooled in an ice bath and quenched with 50 mL of aqueous 2M H2SO4. Water (50 mL) was added to dissolve any remaining solid and the layers were separated. The aqueous layer was extracted with Et2O (2×150 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to yield 1-bromo-2-but-3-enyl-benzene as a light yellow oil. The isolated crude product was carried forward without further purification.

後処理

  1. temperatureat reflux for 1.5 h
  2. temperaturecooled in an ice bath
  3. customquenched with 50 mL of aqueous 2M H2SO4
  4. additionWater (50 mL) was added
  5. dissolutionto dissolve any remaining solid
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with Et2O (2×150 mL)
  8. dry with materialThe combined organic extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-8b9f36c2c6734251a543a45e99dc576f
出典データセット
uspto-grants-2004_08
特許番号
US06777421B2

反応ノート

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