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

HRID 6900

反応式

HRID 6900 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d3006829c64043e1abcf88cb05d868f9
出典データセット
uspto-grants-2006_08
特許番号
US07084165B2

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