Potassium Carbonate → 1-Bromo-2,5-dichloro-3-(2-chloro-6-nitrophenoxy)benzene

HRID 505546노트

반응식

HRID 505546 반응식
[Br:1][C:2]1[C:3]([Cl:10])=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.O>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][C:12]2[C:13]([N+:19]([O-:21])=[O:20])=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:3]=1[Cl:10]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 185552,3-DichloronitrobenzeneHCID 684280893-Bromo-2,5-dichlorophenol

생성물 1

HCID 684255121-Bromo-2,5-dichloro-3-(2-chloro-6-nitrophenoxy)benzene

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

3-bromo-2,5-dichlorophenol (8.0 g, 33 mmol) and 2,3-dichloronitrobenzene (6.4 g, 33 mmol) were dissolved in NMP (30 mL), followed by the addition of potassium carbonate (5.5 g, 40 mmol). The resulting suspension was placed in an oil bath at 120° C. for 7 hours, after which the reaction mixture was diluted with water (150 mL) and extracted with ethyl acetate (2×00 mL). The combined organic fractions were washed with water (3×100 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (330 g) eluting with 0-20% CH2Cl2/hexanes to afford the title compound. 1H NMR (CDCl3) δ 7.98 (dd, J=8.2 Hz, J=1.6 Hz, 1H), 7.79 (dd, J=8.2 Hz, J=1.6 Hz, 1H), 7.44 (dd, J=8.2 Hz, J=8.2 Hz, 1H), 7.40 (d, J=2.2 Hz, 1H), 6.54 (d, J=2.2 Hz, 1H).

후처리

  1. extractionextracted with ethyl acetate (2×00 mL)
  2. washThe combined organic fractions were washed with water (3×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel (330 g)
  7. washeluting with 0-20% CH2Cl2/hexanes

출처 및 근거

ORD 기록
ord-c7fe8dc214444911891a0cee29968636
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781454B2

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