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

HRID 1664142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1664142
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8c4ebe43465d4a82aa695bbf3f038a81
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039458B2

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