Water → 2-(3-Nitrophenoxy)ethanol

HRID 541923노트

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HRID 541923 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][CH2:13][OH:14])([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 108982-Bromoethanol2회HCID 111373-NitrophenolHCID 11430Potassium Carbonate2회

생성물 1

HCID 46689272-(3-Nitrophenoxy)ethanol수율 74.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

A solution of m-nitrophenol (2.0 g, 14 mmol), 2-bromoethanol (1.4 mL, 20 mmol), and potassium carbonate (3.0 g, 22 mmol) in N,N-dimethylformamide (10 mL) was heated at 70° C. for 7 h. The reaction mixture was treated with additional 2-bromoethanol (0.5 mL, 7.2 mmol) and potassium carbonate (1.0 g, 7.2 mmol) and heated at 70° C. for 20 h. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (150 mL). The organic layer was separated and washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to a crude residue. This material was purified by flash column chromatography to give the desired product (1.9 g, 70%) as a white solid. LCMS for C8H10NO4 (M+H)+: m/z=183.9.

후처리

  1. extractionextracted with ethyl acetate (150 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to a crude residue
  7. customThis material was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-b6d43b2d19f94bbdb4c24b9ac8a95d34
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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