Dichloromethane → (2-Bromo-5-fluorophenyl)hydrazine

HRID 1664142ノート

反応式

HRID 1664142 の反応式
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[NH:10][NH2:11].BrC1C=CC(F)=CC=1N.C(Cl)Cl.[OH-].[Na+]>O>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[NH:10][NH2:11]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27733172-Bromo-5-fluoroanilineHCID 21069774(2-Bromo-5-fluorophenyl)hydrazine hydrochloride

生成物 1

HCID 12891829(2-Bromo-5-fluorophenyl)hydrazine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a suspension of (2-bromo-5-fluoro-phenyl)-hydrazine hydrochloride (41 g, 0.17 mol; prepared from 2-bromo-5-fluoroaniline by the method described in U.S. Pat. No. 3,959,309 (1976) p-23, and p-48) in water (300 mL) and CH2Cl2 (200 mL) was added 1N—NaOH (200 mL) until the solution was basic. The CH2Cl2 layer was separated and the aqueous portion was further extracted with CH2Cl2 (150 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated to obtain 33 g (0.16 mol) of the title compound as an off-white powder: HPLC: 0.89 min (AP 97% at 220 nm); 1H NMR (CDCl3, 500 MHz) δ ppm 3.62 (2H, s, NH2), 5.75 (1H, s, NH), 6.37 (1H, m, 5-CH), 6.87 (1H, dd, J=11, 3 Hz, 3-CH), 7.31 (1H, dd, J=8.6, 5.8 Hz, 6-CH); 13C NMR (CDCl3, 125.8 Hz) 8 ppm 100.0 (d, J=29 Hz, 3-CH), 101.4 (d, J=2.9 Hz, 1-C), 106.1 (d, J=23 Hz, 5-CH), 133.1 (d, J=9.6 Hz, 6-CH), 149.1 (d, J=10.6 Hz, 2-C), 163.5 (d, J=244 Hz, 4-CF); LC/MS m/z 205/207 (M+H).

後処理

  1. customThe CH2Cl2 layer was separated
  2. extractionthe aqueous portion was further extracted with CH2Cl2 (150 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8c4ebe43465d4a82aa695bbf3f038a81
出典データセット
uspto-grants-2011_10
特許番号
US08039458B2

反応ノート

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