2-(Dimethylamino)ethanol → 2-(3-bromo-5-nitrophenoxy)-N,N-dimethylethanamine

HRID 2206362

반응식

HRID 2206362 반응식
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][OH:18].[OH-].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)[O:18][CH2:17][CH2:16][N:15]([CH3:19])[CH3:14]

참가 물질

6

반응물 3

HCID 79022-(Dimethylamino)ethanolHCID 14797Potassium HydroxideHCID 445341-Bromo-3,5-dinitrobenzene

생성물 1

HCID 593139932-(3-bromo-5-nitrophenoxy)-N,N-dimethylethanamine수율 57.2%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매

실험 절차

1-Bromo-3,5-dinitrobenzene (1 g, 4.1 mmol), 2-(dimethylamino)ethanol (0.54 g, 6.1 mmol), potassium hydroxide (0.45 g, 8.1 mmol), and water (0.5 mL) in DMF (5 mL) were heated at 80° C. After 20 hours, the reaction mixture was diluted with cold water and extracted with dichloromethane (2×100 mL). The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (stepwise gradient, 2% ethyl acetate in hexanes to ethyl acetate) to give 2-(3-bromo-5-nitrophenoxy)-N,N-dimethylethanamine (669 mg, 57.2% yield) as a brown oil. HPLC: Rt=1.04 min. (PHENOMENEX® Luna 5 micron C18 4.6×30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate=5 mL/min., detection at 254 nm). MS (ES): m/z=290.93 [M+H]+.

후처리

  1. extractionextracted with dichloromethane (2×100 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography (stepwise gradient, 2% ethyl acetate in hexanes to ethyl acetate)

출처 및 근거

ORD 기록
ord-ef9a9b6f39914e55a30293fae4e90ee4
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371328B2

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