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

HRID 29880

반응식

HRID 29880 반응식
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

참가 물질

6

반응물 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 115623-Bromoaniline

생성물 1

HCID 235060153-(4-Fluorophenoxy)aniline

시약·촉매·용매 2

HCID 14829Copper oxide촉매HCID 1049Pyridine용매

반응 조건

온도
210 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-09df41b16d864eddaa7380ff6ca4a6ce
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423043B2

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