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

HRID 636715노트

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HRID 636715 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-120220b3c7d54ca9be48964a1e182d0a
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194454B1

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