Sodium hydride → 1-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester

HRID 1695840

反応式

HRID 1695840 の反応式
[CH2:1]([O:3][C:4]([C:6]1([OH:9])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].C1OCCOCCOCCOCCOC1.[Br:27][C:28]1[CH:33]=[CH:32][C:31](O)=[C:30]([N+:35]([O-:37])=[O:36])[C:29]=1F>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([O:9][C:31]2[CH:32]=[CH:33][C:28]([Br:27])=[CH:29][C:30]=2[N+:35]([O-:37])=[O:36])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 2733706Ethyl 1-hydroxycyclopropane-1-carboxylateHCID 534048764-Bromo-3-fluoro-2-nitrophenol

生成物 1

HCID 583407841-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester収率 51.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of ethyl-1-hydroxycyclopropane carboxylate (2.93 g, 20.5 mmol) in THF (50 mL) was added sodium hydride (60% in mineral oil, 981 mg, 24.5 mmol) under argon atmosphere. After 10 min, 15-crown-5 (0.2 mL) followed by 4-bromo-2-nitro-fluorphenol (4.5 g, 20.5 mmol) were added. The reaction mixture was stirred at room temperature overnight then quenched by the addition of methanol (1.5 mL) and diluted with ethyl acetate. The mixture was washed with brine, and the organic layer was dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography to give 1-(4-bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester (3.51 g).

後処理

  1. additionwere added
  2. customthen quenched by the addition of methanol (1.5 mL)
  3. additiondiluted with ethyl acetate
  4. washThe mixture was washed with brine
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a2f1eed8c7da481fb9f06010ea384b10
出典データセット
uspto-grants-2012_04
特許番号
US08163704B2

関連ノート

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