Reaktion #337101

Reaktionsgleichung

methyl 2-amino-5-bromo-3-methoxybenzoate

methylboronic acid

potassium fluoride

tri-t-butylphosphonium

THF

→

methyl 2-amino-5-methoxy-3-methylbenzoate

Ausbeute 73.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas deoxygenated
2. 2
   EinengenThe reaction mixture was concentrated
3. 3
   Sonstigethe residue purified by column chromatography (silica gel, 0% to 5% EtOAc in hexanes)

Vorschrift

A mixture of methyl 2-amino-5-bromo-3-methoxybenzoate (6.50 g, 25 mmol), methylboronic acid (3.0 g, 50 mmol), potassium fluoride (5.8 g, 100 mmol) and tri-t-butylphosphonium tetrafluoroborte (0.87 g, 3.0 mmol) in THF (200 mL) was deoxygenated and then backfilled with argon. Tris(dibenzylideneacetone)dipalladium(0) (1.43 g, 1.5 mmol), was added and the mixture was heated at 70° C. for 17 h under an argon atmosphere. The reaction mixture was concentrated and the residue purified by column chromatography (silica gel, 0% to 5% EtOAc in hexanes) to afford methyl 2-amino-5-methoxy-3-methylbenzoate (3.55 g, 73%) 1H NMR consistent.

Quelle