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

HRID 1839430

반응식

HRID 1839430 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).

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-f72ff8a8272c46549f0fb40dbe2dd129
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677378B2

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