Potassium Carbonate → Methyl 2-nitro-5-[4-(trifluoromethyl)phenoxy]benzoate

HRID 1075316ノート

反応式

HRID 1075316 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:19]1[CH:20]=[CH:21][C:22]([N+:29]([O-:31])=[O:30])=[C:23]([CH:28]=1)[C:24]([O:26][CH3:27])=[O:25]>CS(C)=O>[F:11][C:8]([F:9])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([O:1][C:19]2[CH:20]=[CH:21][C:22]([N+:29]([O-:31])=[O:30])=[C:23]([CH:28]=2)[C:24]([O:26][CH3:27])=[O:25])=[CH:3][CH:4]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 171018Methyl 5-chloro-2-nitrobenzoate

生成物 1

HCID 13209694Methyl 2-nitro-5-[4-(trifluoromethyl)phenoxy]benzoate収率 85%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

p-Hydroxybenzotrifluoride (0.22 g, 1.36 mmol), powdered potassium carbonate (0.185 g, 1.34 mmol), and methyl 5-chloro-2-nitrobenzoate (0.288 g, 1.34 mmol) were heated at 70° C. under a nitrogen atmosphere in 3 ml of dimethyl sulfoxide. After 50 minutes, an aliquot was quenched in methanolic HCl. (By gas chromatography, the reaction is 45% complete.) After 18 hours (overnight), the reaction mixture was cooled to room temperature, diluted with water, and extracted with ether. The organic extracts are shaken with brine, dried (MgSO4) and concentrated to afford methyl 5-(4-trifluoromethylphenoxy)-2-nitrobenzoate in 85% yield. Gas chromatography showed no starting phenol remained. Step B--Methyl 5-(2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoate

後処理

  1. customan aliquot was quenched in methanolic HCl
  2. wait) After 18 hours (overnight)
  3. additiondiluted with water
  4. extractionextracted with ether
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-dce11846ee5d44c2a50ca89293e122f1
出典データセット
uspto-grants-1983_07
特許番号
US04395570

反応ノート

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