5-Borono-4-chloro-2-methoxybenzoic acid synthesis
- Product Name:5-Borono-4-chloro-2-methoxybenzoic acid
- CAS Number:957066-09-0
- Molecular formula:C8H8BClO5
- Molecular Weight:230.41
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Yield:-
Reaction Conditions:
with potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0);tri tert-butylphosphoniumtetrafluoroborate in tetrahydrofuran;water at 20; for 3 h;Product distribution / selectivity;
Steps:
38.C
N2 was bubbled through a solution of THF (8 ml.) and water (2 mL) containing δ-carboxy^-chloro^-methoxy-phenylboronic acid (460.8 mg, 2 .0 mmol) and δ-bromo^-trifluoromethyl-isonicotinonitrile 1-1 (478 mg, 1.9 mmol) for 10 minutes. K3PO4 (1.2 g, 5.7 mmol), t-Bu3P.HBF4 (82.7 mg, 0.28 mmol), and Pd2dba3 (91.0 mg, 0.1 mmol) were added under N2 atmosphere. The mixture was sealed, stirred at rt for 3 hrs, and diluted with ethyl acetate. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography eluting with 10% MeOH in dichloromethane to give 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzoic acid (301 mg).
References:
WO2008/124610,2008,A1 Location in patent:Page/Page column 120