Stannous chloride dihydrate → 3-(Benzyloxy)-5-bromoaniline

HRID 447053ノート

反応式

HRID 447053 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N+:16]([O-])=O)[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:16])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 147841491-(Benzyloxy)-3-bromo-5-nitrobenzene

生成物 1

HCID 578136263-(Benzyloxy)-5-bromoaniline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

To a solution of 3-benzyloxy-5-bromo-nitrobenzene (27.0 g, 87.60 mmol) in THF (800.0 mL) was added SnCl2.2H2O (99.0 g, 438.30 mmol) and the resulting reaction mixture was heated to reflux at 65° C. for 2 h. The reaction mass was then cooled to 0-5° C. and basified with a saturated solution of NaHCO3 till pH 8 and then extracted with EtOAc (3×1.0 L). The combined organics was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue thus obtained (23.60 g, 95%) was carried forward to the next step without further purification.

後処理

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureThe reaction mass was then cooled to 0-5° C.
  4. extractionextracted with EtOAc (3×1.0 L)
  5. dry with materialThe combined organics was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained (23.60 g, 95%)
  8. customwas carried forward to the next step without further purification

出典と根拠

ORDレコード
ord-3fbaf9c5339e47549666bdb03eed9242
出典データセット
uspto-grants-2013_07
特許番号
US08481544B2

反応ノート

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