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

HRID 2209277

反応式

HRID 2209277 の反応式
[H-].[Na+].[OH:3][C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1.[Br:12][C:13]1[CH:18]=[CH:17][C:16](F)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1>C1COCC1.C1OCCOCCOCCOCCOC1.C(OCC)(=O)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:3][C:4]2([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]2)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 2733706Ethyl 1-hydroxycyclopropane-1-carboxylateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

生成物 1

HCID 583407841-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester収率 66.6%

試薬・触媒・溶媒 3

HCID 3633615-Crown-5触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium hydride (60%, 166 mg, 4.15 mmol) was added to a solution of ethyl 1-hydroxycyclopropanecarboxylate (0.41 mL, 3.59 mmol) in THF (10 mL) at room temperature. After 15 min, 3 drops of 15-crown-5 were added followed by 4-bromo-1-fluoro-2-nitrobenzene (0.42 mL, 3.41 mmol). Mixture was stirred at room temperature for 24 hours. After diluting with 50 mL of ethyl acetate, mixture was quenched by addition of brine (25 mL) and layers were separated. Aqueous phase was extracted with ethyl acetate and combined organics were dried (MgSO4), filtered, and concentrated under reduced pressure. Resulting residue was purified via silica gel column chromatography (0-30% ethyl acetate/hexanes) to yield ethyl 1-(4-bromo-2-nitrophenoxy)cyclopropanecarboxylate 7.20 (750 mg)

後処理

  1. customwas quenched by addition of brine (25 mL) and layers
  2. customwere separated
  3. extractionAqueous phase was extracted with ethyl acetate
  4. dry with materialcombined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customResulting residue was purified via silica gel column chromatography (0-30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-faca75f7960544ebb89e4f0a3c66e48f
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

関連ノート

読み込み中…