Allyl bromide → 5-Allyl-2-bromo-1,3-dimethylbenzene

HRID 237532ノート

反応式

HRID 237532 の反応式
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].C([Li])CCC.[Br:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15](Br)=[CH:14][C:13]=1[CH3:20].C([Cu])#N.[Li+].[Cl-].BrCC=C>O1CCCC1.CCCCCC>[CH2:3]([C:15]1[CH:14]=[C:13]([CH3:20])[C:12]([Br:11])=[C:17]([CH3:18])[CH:16]=1)[CH:1]=[CH2:2]

参加物

9

反応物 6

HCID 7841Allyl bromideHCID 433294Lithium ChlorideHCID 27580472,5-Dibromo-1,3-dimethylbenzeneHCID 178418339ButyllithiumHCID 178418546HCID 178418546、化合物HCID 178418918HCID 178418918、化合物

生成物 1

HCID 866971955-Allyl-2-bromo-1,3-dimethylbenzene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒4 回HCID 8058Hexane溶媒

反応条件

温度
-40 °C

実験手順

To a solution of isopropylmagnesium chloride (6.15 mL of a 2 M solution in tetrahydrofurane) in tetrahydrofurane (75 mL) is added dropwise at 0° C. n-butyllithium (15.4 mL of a 1.6 M solution in n-hexane). The mixture is stirred for 10 minutes, a solution of 2,5-dibromo-1,3-dimethylbenzene (5 g) in tetrahydrofurane (75 mL) is added within 10 minutes. The mixture is stirred for 2 hours, cooled to −40° C. and then CuCN×LiCl (5.5 mL of a 1 M solution in tetrahydrofurane) is added dropwise. After stirring for 5 minutes 3-bromopropene (6.6 mL) is added dropwise, the mixture is stirred for 1 hour, warmed to room temperature and stirred for further 12 hours. Then the reaction is quenched by addition of saturated aqueous NH4Cl solution. The mixture is extracted with diethylether, the organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (dichloromethane) to give the title compound. Yield: 3.76 g; LC (method 8): tR=0.83 min; Mass spectrum (ESI+): m/z=225 [M+H]+.

後処理

  1. stirringThe mixture is stirred for 2 hours
  2. additionis added dropwise
  3. stirringthe mixture is stirred for 1 hour
  4. temperaturewarmed to room temperature
  5. stirringstirred for further 12 hours
  6. customThen the reaction is quenched by addition of saturated aqueous NH4Cl solution
  7. extractionThe mixture is extracted with diethylether
  8. dry with materialthe organic phase is dried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue is chromatographed on silica gel (dichloromethane)

出典と根拠

ORDレコード
ord-c595b52dfdca4e89a16b78074e810d5e
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

反応ノート

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