Potassium Hydroxide → 2-(Benzyloxy)-3-fluorophenol

HRID 39016ノート

反応式

HRID 39016 の反応式
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:17]1CCOCC1.[OH-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 532169822-(Benzyloxy)-1-chloro-3-fluorobenzene

生成物 1

HCID 107751752-(Benzyloxy)-3-fluorophenol

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2-(benzyloxy)-1-chloro-3-fluorobenzene (3 g, 12.71 mmol), dioxane (6 ml), KOH (0.78 g, 14 mmol), water (6 ml), Tris(dibenzylideneacetone)dipalladium (0.12 g, 0.13 mmol) and 2-di-tertbutylphosphine-2,4,6-triisopropylbiphenyl (0.22 g, 0.51 mmol) was flushed with N2 and heated under microwave radiation at 120° C. for 7 min. HCl (1 N) was added and the solution was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to dryness. Flash column chromatography (isooctane/EtOAc) yielded the title compound (1.86 g). MS m/z (rel. intensity, 70 eV) 218 (M+, 4), 92 (8), 91 (bp), 65 (13), 51 (9).

後処理

  1. customwas flushed with N2
  2. additionHCl (1 N) was added
  3. extractionthe solution was extracted with EtOAc
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-9ab18781cc814d62921fc9a44e38d60c
出典データセット
uspto-grants-2013_09
特許番号
US08524766B2

反応ノート

読み込み中…