Boron tribromide → 2-(3-Isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile

HRID 636715ノート

反応式

HRID 636715 の反応式
[CH:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[O:23]C)[O:7][C:8]1[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:9]=1[C:10]#[N:11])([CH3:3])[CH3:2].B(Br)(Br)Br>ClCCl>[CH:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[OH:23])[O:7][C:8]1[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:9]=1[C:10]#[N:11])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 155236442-(3-Isopropyl-4-methoxy-phenoxy)-3-methyl-5-nitrobenzonitrile

生成物 1

HCID 155236452-(3-Isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile収率 72.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a cooled (−78° C.), stirred solution of 2-(3-isopropyl-4-methoxy-phenoxy)-3-methyl-5-nitrobenzonitrile (308 mg) in dichloromethane (5 mL) was added boron tribromide (0.31 mL) dropwise. The reaction was allowed to warm to RT and stirred for 1 h, quenched with water and stirred for 20 min. The reaction was extracted with ethyl acetate, the organic phase washed with water, saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo. Flash chromatography (20% ethyl acetate/hexanes) on silica gel afforded 2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile as a yellow oil (215 mg).

後処理

  1. temperatureto warm to RT
  2. customquenched with water
  3. stirringstirred for 20 min
  4. extractionThe reaction was extracted with ethyl acetate
  5. washthe organic phase washed with water, saturated aqueous brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-120220b3c7d54ca9be48964a1e182d0a
出典データセット
uspto-grants-2001_02
特許番号
US06194454B1

反応ノート

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