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

HRID 1075316노트

반응식

HRID 1075316 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-dce11846ee5d44c2a50ca89293e122f1
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04395570

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