2-(3,4-Dichlorophenoxy)-5-fluorobenzaldehyde → 2-(3,4-Dichlorophenoxy)-5-fluoro-benzoic acid

HRID 6900

반응식

HRID 6900 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][C:6]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:7]=1[CH:8]=[O:9].CC(C)=[O:21].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][C:6]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:7]=1[C:8]([OH:21])=[O:9]

참가 물질

4

반응물 2

HCID 220192712-(3,4-Dichlorophenoxy)-5-fluorobenzaldehydeHCID 131709961Jones' reagent

생성물 1

HCID 220192772-(3,4-Dichlorophenoxy)-5-fluoro-benzoic acid

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
25 °C

실험 절차

Alternatively, a solution of 4.28 g (15 mmol) of 2-(3,4-dichloro-phenoxy)-5-fluorobenzaldehyde (Preparation no. 5) in 25 mL of acetone was cooled to 5–10° C. and treated via syringe with 5.8 mL (15.6 mmol) of 2.67 M Jones reagent*. After 1 hr at this temperature, the reaction was quenched with 8 mL of isopropanol, allowed to warm to 25° C., and filtered through a pad of d.e. The filtrate was concentrated in vacuo to approximately ¼ volume, diluted with water and extracted several times with CHCl3. The organic layers were washed with water, then with saturated NaCl and finally dried over MgSO4 and concentrated to provide 2-(3,4-dichlorophenoxy)-5-fluoro-benzoic acid as a tan solid, 4.19 g. 1H-nmr (CDCl3, 400 MHz, δ): 7.78 (dd, 1H), 7.38 (d, 1H), 7.27 (m, 1H), 6.98 (m, 2H), 6.81 (dd, 1H). *Jones reagent was prepared from 13.4 g of chromium trioxide and 11.5 mL of concentrated H2SO4, diluted to a final volume of 50 mL with H2O.

후처리

  1. customthe reaction was quenched with 8 mL of isopropanol
  2. filtrationfiltered through a pad of d.e
  3. concentrationThe filtrate was concentrated in vacuo to approximately ¼ volume
  4. additiondiluted with water
  5. extractionextracted several times with CHCl3
  6. washThe organic layers were washed with water
  7. dry with materialwith saturated NaCl and finally dried over MgSO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d3006829c64043e1abcf88cb05d868f9
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084165B2

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