Aniline → HCID 68157084、化合物

HRID 242768

反応式

HRID 242768 の反応式
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[C:12]1([NH2:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

7

反応物 3

HCID 6115AnilineHCID 10796Cesium carbonateHCID 2318282-Bromo-3-nitrotoluene

生成物 1

HCID 68157084HCID 68157084、化合物収率 93%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 634876Binap, (A+-)-触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2-bromo-1-methyl-3-nitrobenzene (1.0 g, 4.63 mmol), phenylamine (506 μL, 5.56 mmol), Cs2CO3 (2.11 g, 6.48 mmol) and (R)-BINAP (5 mol %, 143 mg, 0.23 mmol) in toluene (10 mL) was degassed with a stream of nitrogen prior to addition of Pd(OAc)2 (25 mg, 0.11 mmol) and was stirred at 110° C. under a nitrogen atmosphere for 20 h. After cooling to RT, the mixture was partitioned between EtOAc and water. The organic layer was washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-35% DCM in cyclohexane) affording (2-Methyl-6-nitrophenyl)phenylamine as a red solid (981 mg, 93%). LCMS: RT 3.88 min [M+H]+ 229.1

後処理

  1. customwas degassed with a stream of nitrogen
  2. temperatureAfter cooling to RT
  3. customthe mixture was partitioned between EtOAc and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-35% DCM in cyclohexane)

出典と根拠

ORDレコード
ord-d53a55bb2ef14a829cddb58d6acce357
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

関連ノート

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