Propiolic Acid → 4-Bromo-3,5-dimethylphenyl propiolate

HRID 1483185ノート

反応式

HRID 1483185 の反応式
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[C:11](O)(=[O:14])[C:12]#[CH:13].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:11]([O:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[C:3]([CH3:10])[CH:4]=1)(=[O:14])[C:12]#[CH:13]

参加物

6

反応物 3

HCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 819704-Bromo-3,5-dimethylphenol

生成物 1

HCID 725452334-Bromo-3,5-dimethylphenyl propiolate収率 51%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of 4-bromo-3,5-dimethylphenol (40.87 g, 203.3 mmol) and propiolic acid (20.91 g, 298.5 mmol) in CH2Cl2 (400 mL) was added DCC (50.78 g, 246.1 mmol) in CH2Cl2 (100 mL) and DMAP (0.82 g, 6.7 mmol) at 0° C. The mixture was stirred at room temperature for 3 h and filtered. The filtrate was concentrated and purified by silica gel column chromatography (hexanes:EtOAc:CH2Cl2=20:1:10). The fractions containing the desired compound were concentrated. To the concentrate added hexane and the precipitated solid was collected by filtration. The solid was washed with hexane and dried to give the title compound 6-1 (26.12 g, 51% yield) as a white solid.

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography (hexanes:EtOAc:CH2Cl2=20:1:10)
  4. additionThe fractions containing the desired compound
  5. concentrationwere concentrated
  6. additionTo the concentrate added hexane
  7. filtrationthe precipitated solid was collected by filtration
  8. washThe solid was washed with hexane
  9. customdried

出典と根拠

ORDレコード
ord-53954c35f7804a46a5de309dfd918267
出典データセット
uspto-grants-2016_08
特許番号
US09416121B2

反応ノート

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