Water → 2-Bromo-4-fluoro-6-nitroaniline

HRID 53725

反応式

HRID 53725 の反応式
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:12][C:7]1[C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=[C:2]([F:1])[CH:8]=1

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 677694-Fluoro-2-nitroaniline

生成物 1

HCID 2920042-Bromo-4-fluoro-6-nitroaniline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

6-Bromo-4-fluoro-2-nitroaniline was prepared using an adaptation of the method of Mitchell et al., J. Org. Chem. 44: 4733 (1979). To a solution of 4-fluoro-2-nitroaniline (500 mg, 3.2 mmol) in dry DMF (16 mL) under N2 was added dropwise a solution of N-bromosuccinimide (570 mg, 3.2 mmol) in dry DMF (16 mL). The reaction was allowed to stir 24 h. The solution was then poured into 100 mL H2O and this aqueous phase extracted with 4×25 mL CH2Cl2. The combined organic phases were washed with 3×4 mL H2O and dried (MgSO4). The MgSO4 was vacuum filtered and the solvent rotary evaporated to yield a brown oil which crystallized on standing. 642 mg (85.4%). 1H NMR (CDCl3) δ 6.51 (br s, 2H NH2), 7.58 (dd, JH4-3 -3 Hz, JH4-F =6.5 Hz, H-4), 7.92 (dd, JH3-F =3 Hz, JH3-F =8.7 Hz, H-3).

後処理

  1. extractionthis aqueous phase extracted with 4×25 mL CH2Cl2
  2. washThe combined organic phases were washed with 3×4 mL H2O
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent rotary evaporated
  6. customto yield a brown oil which
  7. customcrystallized

出典と根拠

ORDレコード
ord-062ecdfb9527417fbd24c7be4f4f6ae9
出典データセット
uspto-grants-1997_04
特許番号
US05620979

関連ノート

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