4-Bromo-2-chlorobenzonitrile → (4-Bromo-2-chlorophenyl)methanamine

HRID 40273

Reaktionsgleichung

Reaktionsgleichung von HRID 40273
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([Cl:10])[CH:3]=1

Komponenten

3

Edukt 1

HCID 70104204-Bromo-2-chlorobenzonitrile

Produkt 1

HCID 25258775(4-Bromo-2-chlorophenyl)methanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a solution of 4-bromo-2-chlorobenzonitrile (2500 mg, 11549 μmol) in THF (20 mL) at 0° C. was added borane-methyl sulfide complex, 2.0 m sol in THF (28873 μl, 57747 μmol). Ice bath removed and reaction stirred overnight warming to 23° C. Reaction cooled to 0° C. and quenched with MeOH (15 mL). Reaction then partitioned between CHCl3 (100 mL) and 1M NaOH (100 mL). Organic dried with brine and MgSO4. Organic then concentrated to an oil under reduced pressure and purified on silica (80 g) eluting with 0>6% 2M NH3 in MeOH/DCM and product isolated as a colorless oil. MS (ESI pos. ion) m/z: 220/222 (MH+). Calc'd exact mass for C7H7BrClN: 219/221

Aufarbeitung

  1. customIce bath removed
  2. customreaction
  3. customReaction
  4. temperaturecooled to 0° C.
  5. customquenched with MeOH (15 mL)
  6. customReaction
  7. customthen partitioned between CHCl3 (100 mL) and 1M NaOH (100 mL)
  8. dry with materialOrganic dried with brine and MgSO4
  9. concentrationOrganic then concentrated to an oil under reduced pressure
  10. custompurified on silica (80 g)
  11. washeluting with 0>6% 2M NH3 in MeOH/DCM and product
  12. customisolated as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-bfd7899b801142a391163ea156ad25e4
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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