Oxalyl chloride → 6-Bromo-2-naphthoyl chloride

HRID 55752

Reaktionsgleichung

Reaktionsgleichung von HRID 55752
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([Cl:18])=[O:14])[CH:6]=[CH:5]2

Komponenten

5

Edukt 2

HCID 65578Oxalyl chlorideHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Produkt 1

HCID 218796066-Bromo-2-naphthoyl chlorideAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. dissolutionComplete dissolution
  2. concentrationThe reaction mixture was concentrated
  3. additiondichloromethane (100 mL) was added
  4. customthe solvent was evaporated again

Quellen und Nachweise

ORD-Eintrag
ord-8e890819485b476c9aa40cc3b93e3f03
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09433609B2

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