Ethanol → 3-Iodo-4-methoxyaniline

HRID 1632107ノート

反応式

HRID 1632107 の反応式
N#N.[Cl-].[NH4+].C(O)C.[I:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[O:18][CH3:19]>[Fe].O>[I:8][C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[O:18][CH3:19]

参加物

7

反応物 4

HCID 702EthanolHCID 947NitrogenHCID 25517Ammonium ChlorideHCID 948062-Iodo-1-methoxy-4-nitrobenzene

生成物 1

HCID 220545963-Iodo-4-methoxyaniline収率 88%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

In a 3-neck 250 mL round-bottomed flask equipped with a stir bar, condenser and N2 lines was placed iron powder (3.50 g, 62.7 mmol), ammonium chloride (4.88 g, 91.3 mmol), ethanol (72 mL) and water (23 mL). The mixture was heated to 85° C. and then 2-iodo-1-methoxy-4-nitro-benzene (5.0 g, 17.9 mmol) was added portion wise over a period of about 2 minutes. The mixture was allowed to stir at 85° C. for 2 hours and then filtered through Celite. The Celite was washed with EtOH (100 mL) and the filtrate was concentrated. To the concentrated material was added water (100 mL) and ethyl acetate (150 mL). The organic portion was removed and the aqueous portion was re-extracted with ethyl acetate (150 mL). The organic portions were combined, washed with brine (150 mL), dried (MgSO4) and concentrated. The residue was purified by column chromatography utilizing 50% EtOAc/hexanes as the eluent to produce 3.92 g of I-252 as a brown semi-solid in 88% yield. MS (ESI+): 250.1 (M+1).

後処理

  1. customIn a 3-neck 250 mL round-bottomed flask equipped with a stir bar, condenser
  2. filtrationfiltered through Celite
  3. washThe Celite was washed with EtOH (100 mL)
  4. concentrationthe filtrate was concentrated
  5. additionTo the concentrated material was added water (100 mL) and ethyl acetate (150 mL)
  6. customThe organic portion was removed
  7. extractionthe aqueous portion was re-extracted with ethyl acetate (150 mL)
  8. washwashed with brine (150 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customThe residue was purified by column chromatography
  12. customto produce 3.92 g of I-252 as a brown semi-solid in 88% yield

出典と根拠

ORDレコード
ord-bc4599240ec944d584c769d7f4dac307
出典データセット
uspto-grants-2014_07
特許番号
US08791267B2

反応ノート

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