Ammonium Chloride → 5-Bromo-3-fluoro-2-methoxyaniline

HRID 889426

反応式

HRID 889426 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[C:5]([O:9][CH3:10])=[C:6]([F:8])[CH:7]=1.[Cl-].[NH4+]>CCO.O.ClCCl.[Zn]>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH3:10])=[C:4]([CH:3]=1)[NH2:11]

参加物

7

反応物 2

HCID 25517Ammonium ChlorideHCID 5571594-Bromo-2-fluoro-6-nitroanisole

生成物 1

HCID 534184245-Bromo-3-fluoro-2-methoxyaniline収率 82.1%

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

5-Bromo-1-fluoro-2-methoxy-3-nitrobenzene (1.0 g, 4.0 mmol), zinc (2.62 g, 40.0 mmol) and ammonium chloride (2.14 g, 40.0 mmol) in EtOH (20 mL) and water (12 mL) were heated at 80° C. for 10 minutes and then stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane (100 mL) and water (60 mL), and filtered through CELITE®. The organic phase was dried over sodium sulfate and filtered and then concentrated to afford Intermediate 25A (723 mg, 82% yield) as a gray solid. HPLC: Rt=1.3 min. (PHENOMENEX® Luna 5 micron C18 4.6×30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate=5 mL/min., detection at 254 nm). MS (ES): m/z=222.0 [M+H]+.

後処理

  1. filtrationfiltered through CELITE®
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-a225c5b587444c808d224327e708f69c
出典データセット
uspto-grants-2012_08
特許番号
US08252795B2

関連ノート

読み込み中…