Acetic Acid → 2-(Benzyloxy)-4-fluoroaniline

HRID 1289367ノート

反応式

HRID 1289367 の反応式
C(O)(=O)C.[F:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1>C(OCC)(=O)C.[Fe]>[F:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:7]=1

参加物

5

反応物 2

HCID 176Acetic AcidHCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

生成物 1

HCID 167713362-(Benzyloxy)-4-fluoroaniline収率 70.4%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
76 °C

実験手順

To a mixture of iron powder (90.36 g, 1.62 mol) and acetic acid (10%, 400 mL) at 80° C. was added a solution of the title compound of Step A (40 g, 0.162 mol) in ethyl acetate (200 mL) dropwise with vigorous stirring. The reaction mixture was stirred further at 76° C. for 1 h. After the reaction was complete, the hot reaction mixture was filtered through Celite® (200 g) and the filter cake was washed with ethyl acetate (1000 mL). The filtrate was washed with water (3×200 mL), sodium bicarbonate solution (5%, 3×200 mL), dried (MgSO4) and concentrated to give the crude product. The product was purified by flash chromatography to give 24.76 g of the title compound of Step B. 1H NMR (CDCl3, 400 MHz): δ7.41 (m,5H), 6.60 (m,3H), 5.04 (s,2H).

後処理

  1. filtrationthe hot reaction mixture was filtered through Celite® (200 g)
  2. washthe filter cake was washed with ethyl acetate (1000 mL)
  3. washThe filtrate was washed with water (3×200 mL), sodium bicarbonate solution (5%, 3×200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThe product was purified by flash chromatography

出典と根拠

ORDレコード
ord-08479fc24d0343a9b5cdf9355c466806
出典データセット
uspto-grants-1998_05
特許番号
US05750471

反応ノート

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