Nitroethane → 1-(2,5-Difluorophenyl)-2-nitropropene

反応式

[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.[N+:11]([CH2:14][CH3:15])([O-:13])=[O:12].C1(N)CCCCC1>C(O)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=[C:14]([N+:11]([O-:13])=[O:12])[CH3:15]

参加物

反応条件

温度: 80 °C

実験手順

A mixture of 2,5-difluorobenzaldehyde (25.0 g, 0.176 mol), nitroethane (26.41 g, 0.352 mol) and cyclohexylamine (17.45 g, 0.176 mol) in 150 mL of acetic acid was stirred at 80° C. overnight. After cooling to rt the solvent was evaporated, the residue was purified by column chromatography (silica-gel, CH2Cl2/acetone=19/1 v/v) to give a yellow solid product, 28.5 g, 81.3% yield. MS: 197.6 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 7.94 (s, 1H), 7.46-7.43 (m, 1H), 7.41-7.35 (m, 2H), 2.31 (s, 3H).

後処理

temperatureAfter cooling to rt the solvent
customwas evaporated
customthe residue was purified by column chromatography (silica-gel, CH2Cl2/acetone=19/1 v/v)
customto give a yellow solid product, 28.5 g, 81.3% yield

出典と根拠

ORDレコード: ord-1c9a8319490d48369f38e5846bbd8c50
出典データセット: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08822500B2

反応ノート

読み込み中…

参加物

反応物 3

HCID 6587Nitroethane

HCID 7965Cyclohexylamine

HCID 1376632,5-Difluorobenzaldehyde

生成物 1

HCID 666905281-(2,5-Difluorophenyl)-2-nitropropene収率 81.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度: 80 °C

実験手順

後処理

temperatureAfter cooling to rt the solvent
customwas evaporated
customthe residue was purified by column chromatography (silica-gel, CH2Cl2/acetone=19/1 v/v)
customto give a yellow solid product, 28.5 g, 81.3% yield

出典と根拠

ORDレコード: ord-1c9a8319490d48369f38e5846bbd8c50
出典データセット: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08822500B2

反応ノート

読み込み中…