4-Fluorophenol → 3-(4-Fluorophenoxy)aniline

HRID 29880

反応式

HRID 29880 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]=O.N1C=CC=CC=1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:2]2[CH:3]=[C:4]([NH2:5])[CH:6]=[CH:7][CH:8]=2)=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 115623-Bromoaniline

生成物 1

HCID 235060153-(4-Fluorophenoxy)aniline

試薬・触媒・溶媒 2

HCID 14829Copper oxide触媒HCID 1049Pyridine溶媒

反応条件

温度
210 °C

実験手順

In a dry microwave vessel with stir bar, 3-bromoaniline (316 μL, 0.029 mol) and 4-flourophenol (716 mg, 0.064 mol) were added to anhydrous pyridine (10 mL) under nitrogen. To this was added potassium carbonate (1.6 g, 120 mol) and copper(II) oxide (1.2 g, 145 mol). The microwave vessel was sealed then heated in the microwave at normal absorbance at 210° C. for 40 min. The cooled reaction was filtered through a bed of Celite with ethyl acetate. The filtrate was then washed 3 times with concentrated aqueous NaHSO4 and twice with concentrated aqueous NaCl. The organic layer was then dried over magnesium sulfate, filtered and concentrated. Purification over silica using an eluent of hexane and ethyl acetate with a gradient of 0-23% ethyl acetate over 45 min gave 3-(4-fluoro-phenoxy)-phenylamine.

後処理

  1. customThe microwave vessel was sealed
  2. customThe cooled reaction
  3. filtrationwas filtered through a bed of Celite with ethyl acetate
  4. washThe filtrate was then washed 3 times with concentrated aqueous NaHSO4
  5. dry with materialThe organic layer was then dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification over silica using an eluent of hexane and ethyl acetate with a gradient of 0-23% ethyl acetate over 45 min

出典と根拠

ORDレコード
ord-09df41b16d864eddaa7380ff6ca4a6ce
出典データセット
uspto-grants-2008_09
特許番号
US07423043B2

関連ノート

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