Reaktion #84030

ord-8e890819485b476c9aa40cc3b93e3f03

Reaktionsgleichung

O=C(O)c1ccc2cc(Br)ccc2c1
6-bromo-2-naphthoic acid
O=C(Cl)C(=O)Cl
Oxalylchloride
O=C(Cl)c1ccc2cc(Br)ccc2c1
6-bromo-2-naphthoyl chloride
Ausbeute 100.1%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISSOLUTIONComplete dissolution
  2. 2
    EinengenThe reaction mixture was concentrated
  3. 3
    workup.ADDITIONdichloromethane (100 mL) was added
  4. 4
    Sonstigethe solvent was evaporated again

Vorschrift

6-bromo-2-naphthoic acid (72.3 g, 282 mmol, 1.0 equiv.) was suspended in dichloromethane (600 mL) and DMF (catalytic, 5 drops) was added. Oxalylchloride (71.6 g, 564 mmol, 2.0 equiv.) was added portion wise during 1 hour. The reaction mixture was stirred overnight with a CaCl2 drying tube mouthed on the flask. Complete dissolution occurred. The reaction mixture was concentrated, dichloromethane (100 mL) was added and the solvent was evaporated again, yielding 6-bromo-2-naphthoyl chloride (76.1 g, 100%) as an oil which was used as such in next step.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09433609B2uspto-grants-2016_09