1-(1,1-Difluoroethyl)-3-nitrobenzene → 3-(1,1-Difluoroethyl)aniline

HRID 1640139ノート

反応式

HRID 1640139 の反応式
[F:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1)([F:4])[CH3:3]>CC(O)=O.CCOC(C)=O.[Zn]>[F:1][C:2]([C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)([F:4])[CH3:3]

参加物

5

反応物 1

HCID 108778561-(1,1-Difluoroethyl)-3-nitrobenzene

生成物 1

HCID 234450923-(1,1-Difluoroethyl)aniline

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-(1,1-difluoroethyl)-3-nitrobenzene (2.75 g, 14.7 mmol) in AcOH (30 mL) was added zinc (10.0 g, 153 mmol). The reaction mixture was allowed to stir at rt overnight. The mixture was diluted with EtOAc (40 mL) and filtered through Celite. The filtrate was concentrated. The residue was diluted with DCM (20 mL), washed with saturated NaHCO3 (20 mL) and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(1,1-difluoroethyl)benzenamine as light brown oil. 1H NMR (300 MHz, DMSO) δ 7.21 (dd, 1H), 6.89 (s, 1H), 6.80 (d, 1H), 6.79 (d, 1H), 186 (t, 3H); LCMS: ES+ 158.1.

後処理

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. additionThe residue was diluted with DCM (20 mL)
  4. washwashed with saturated NaHCO3 (20 mL) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-3c60a7b919394ee2ae5c20f9e6d43e43
出典データセット
uspto-grants-2012_02
特許番号
US08110687B2

反応ノート

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