反応 #48712

反応方程式

hydrochloric acid

aluminum chloride

1-benzyloxy-3-bromo-5-fluoro-benzene

dimethylaniline

→

desired compound

収率 66.6%

3-bromo-5-fluoro-phenol

収率 66.6%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGRemove ice-bath and stir 2 hours
2. 2
   洗浄Separate layers and wash the organic layer with 2N hydrochloric acid (4×50 mL)
3. 3
   抽出Extract the organic layer with 3N potassium hydroxide (4×50 mL)
4. 4
   抽出Acidify with 5N hydrochloric acid and extract with dichloromethane (3×50 mL)
5. 5
   乾燥Dry the dichloromethane layer (sodium sulfate)
6. 6
   濃縮concentrate

実験手順

Add aluminum chloride (13.51 g, 101.38 mmol) to 1-benzyloxy-3-bromo-5-fluoro-benzene (9.50 g, 33.79 mmol, prepared according to WO 03/101956) and dimethylaniline (40.96 g, 337.92 mmol) in dichloromethane (84 mL) at −0° C. under nitrogen and stir 10 minutes. Remove ice-bath and stir 2 hours. Add 60 mL 2N hydrochloric acid dropwise. Separate layers and wash the organic layer with 2N hydrochloric acid (4×50 mL). Extract the organic layer with 3N potassium hydroxide (4×50 mL). Acidify with 5N hydrochloric acid and extract with dichloromethane (3×50 mL). Dry the dichloromethane layer (sodium sulfate) and concentrate to give 4.3 g (66.6%) of the desired compound as an oil.

出典