Iodine → 4-Iodo-2-n-propylaniline

HRID 276248ノート

反応式

HRID 276248 の反応式
[CH2:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])[CH2:2][CH3:3].C([O-])(O)=O.[Na+].[I:16]I>CO.O>[I:16][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH2:1][CH2:2][CH3:3])[CH:10]=1

参加物

6

反応物 3

HCID 807IodineHCID 157592-PropylanilineHCID 516892Sodium Bicarbonate

生成物 1

HCID 105155324-Iodo-2-n-propylaniline収率 98%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

反応条件

温度
10 °C

実験手順

To a solution of 2-n-propylaniline in MeOH (25 mL) was added a solution of NaHCO3 (5.0 g, 59.5 mmol) in H2O (25 mL). Iodine (8.4 g, 33.3 mmol) was added portionwise over 70 min. while maintaining the temp. at 10° C., then the mixture was allowed to stir at 10° C. for 30 min. The resulting mixture was diluted with H2O (30 mL) and extracted with EtOAc (4×40 mL). The combined organic layers were sequentially washed with a 5% Na2S2O3 solution (30 mL) and a saturated NaHCO3 solution (30 mL), dried (Na2SO4), and concentrated under reduced pressure to give 4-iodo-2-n-propylaniline (9.4 g, 98%): TLC (20% EtOAc/hex) Rf0.43. This material was used in the next step without further purification.

後処理

  1. temperaturewhile maintaining the temp
  2. customat 10° C.
  3. extractionextracted with EtOAc (4×40 mL)
  4. washThe combined organic layers were sequentially washed with a 5% Na2S2O3 solution (30 mL)
  5. dry with materiala saturated NaHCO3 solution (30 mL), dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-69ae2d4f7ec34da68b4a3f828bf7c267
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

反応ノート

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