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

HRID 505546ノート

反応式

HRID 505546 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c7fe8dc214444911891a0cee29968636
出典データセット
uspto-grants-2010_08
特許番号
US07781454B2

反応ノート

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