Hydrochloric Acid → 4-Bromo-3-[2-(2,4-dichlorophenyl)-ethoxy]-5-methoxy-benzoic Acid

HRID 967434ノート

反応式

HRID 967434 の反応式
[Br:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22].[C:23](=O)([O-])[O-].[K+].[K+].CBr.Cl>CN(C=O)C.O>[Br:1][C:2]1[C:10]([O:11][CH3:23])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6323Methyl BromideHCID 11430Potassium CarbonateHCID 220524124-Bromo-3-[2-(2,4-dichlorophenyl)ethoxy]-5-hydroxybenzoic acid

生成物 1

HCID 220523294-Bromo-3-[2-(2,4-dichlorophenyl)-ethoxy]-5-methoxy-benzoic Acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

0.2 g (0.49 mmol) of 4-Bromo-3-[2-(2,4-dichlorophenyl)-ethoxy]-5-hydroxy-benzoic acid was dissolved in 5 ml DMF and 0.272 mg (1.97 mmol) of potassium carbonate was added. The solution was cooled to 0° C. and 0.699 g (4.9 mmol) methyl bromide was added. The solution was stirred for 16 h at RT. The solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/1). The resulting compound was dissolved in 10 ml dioxan and 1 ml water. 2N aqueous NaOH was added to the solution to give a pH of 13. The reaction solution was heated at 60° C. for 4 h. 5 ml water was added, followed by concentrated hydrochloric acid to give a pH of 1-2, whereupon the product precipitated from solution. The suspension was stirred for 30 min, then the product was filtered off and dried under reduced pressure.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/1)
  3. dissolutionThe resulting compound was dissolved in 10 ml dioxan
  4. addition2N aqueous NaOH was added to the solution
  5. customto give a pH of 13
  6. temperatureThe reaction solution was heated at 60° C. for 4 h
  7. customto give a pH of 1-2
  8. customwhereupon the product precipitated from solution
  9. stirringThe suspension was stirred for 30 min
  10. filtrationthe product was filtered off
  11. customdried under reduced pressure

出典と根拠

ORDレコード
ord-c4f60b8355684007bac4d690fa6f864e
出典データセット
uspto-grants-2005_10
特許番号
US06953857B2

反応ノート

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