1-Bromo-2-Chloroethane → HCID 22326897, 화합물

HRID 601032노트

반응식

HRID 601032 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].Br[CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:16][CH2:15][CH2:14][O:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[O:2][CH3:1]

참가 물질

5

반응물 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 767382-Methoxy-4-nitrophenol

생성물 1

HCID 22326897HCID 22326897, 화합물수율 56.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 2-methoxy-4-nitro-phenol (2.50 g, 14.8 mmol), 1-bromo-2-chloro-ethane (1.35 mL, 16.3 mmol) and potassium carbonate (4.08 g, 29.6 mmol) in DMF (50 mL) in a sealed tube was heated at 90° C. for 18 h. The reaction was cooled and filtered, washing with ethyl acetate. The filtrate was washed with sodium bicarbonate, water (4 times) and brine, was dried (sodium sulfate) and evaporated. Purification by flash chromatography (SiO2) eluted with 35:65 ethyl acetate:hexanes provided 1-(2-chloro-ethoxy)-2-methoxy-4-nitro-benzene (1.93 g, 56% yield) as an off-white solid. 1H-NMR (DMSO-d6, 500 MHz) 7.89 (dd, 1H), 7.76 (d, 1H), 7.21 (d, 1H), 4.41 (t, 2H), 4.00 (t, 2H), 3.90 (s, 3H) ppm; HPLC (Method A) 3.781 min.

후처리

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washwashing with ethyl acetate
  4. washThe filtrate was washed with sodium bicarbonate, water (4 times) and brine
  5. dry with materialwas dried (sodium sulfate)
  6. customevaporated
  7. customPurification by flash chromatography (SiO2)
  8. washeluted with 35:65 ethyl acetate

출처 및 근거

ORD 기록
ord-86fe6a3a92ec425d8b5f686d0b34f3d5
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902239B2

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