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

HRID 2206362

反応式

HRID 2206362 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-ef9a9b6f39914e55a30293fae4e90ee4
出典データセット
uspto-grants-2016_06
特許番号
US09371328B2

関連ノート

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