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Acetic Acid → Methyl 1-(4-bromophenyl)cyclopropane-1-carboxylate

HRID 861025
ノート
印刷プレビュー

反応式

HRID 861025 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:13].[Na+].C[C:16](O)=[O:17]>CCO.[Cl-].[Na+].O>[CH3:16][O:17][C:11]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1)=[O:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

生成物 1

HCID 46739795Methyl 1-(4-bromophenyl)cyclopropane-1-carboxylate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 57417360Sodium chloride; water溶媒
このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート

反応条件

温度
100 °C

実験手順

To a solution of -(4-bromo-phenyl)-cyclopropanecarbonitrile from Step 1 in EtOH (0.2M) was added NaOH 25% (10 eq.). The mixture was stirred for 6 h at 100° C., quenched with AcOH (20 eq.), poured in brine, extracted with EtOAc (2×). The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was dissolved in CH2Cl2 and diazomethane was added portionwise until the esterification was completed by TLC. Flash chromatography (Hex:EtOAc; 9:1) afforded the title compound as a colorless oil.

後処理

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. additiondiazomethane was added portionwise until the esterification

出典と根拠

ORDレコード
ord-b49024aea32b4a2eb2534955fd7ceac2
出典データセット
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07153968B2

反応ノート

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