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ChemicalBook CAS DataBase List Methyl 3-borono-5-chlorobenzoate
957120-26-2

Methyl 3-borono-5-chlorobenzoate synthesis

1synthesis methods
408492-29-5 Synthesis
3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester

408492-29-5
26 suppliers
$45.00/25mg

-

Yield:957120-26-2 7 g

Reaction Conditions:

with sodium periodate;ammonium acetate in water;acetone at 25; for 2 h;

Steps:

1 Step 1: [3-chloro-5-(methoxycarbonyl)phenyl]boronic acid

To a suspension of 12 g (40 mmol) methyl 3-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate in 30 mL acetone and 30 mL 0 were added 17.3 g (80.9 mmol) sodium periodate and 6.24 g (80.9 mmol) ammonium acetate. The mixture was stirred at 25 °C for 2 h and then filtered through celite. The filtrate was evaporated. The residue was diluted with 200 mL ethyl acetate and washed with 100 mL H2O. The organic phase was washed with brine, dried over anhydrous Na2S04, filtered and concentrated in vacuum. The crude product was triturated with 10 mL petroleum ether at 15 °C for 20 min. The mixture was filtered and the residue dried under reduced pressure to obtain 7 g [3- Chloro-5-(methoxycarbonyl)phenyl]boronic acid as a white solid. -NMR (400 MHz, CDCI3): d = 8.72 (s, 1H), 8.35 (s, 1H), 8.27 (s, 1H), 4.02 (s, 3H). Referenced to the signal of trace CHCI3 at 7.25 ppm. Measured using a Varian 400MR NMR machine.

References:

WO2019/197468,2019,A1 Location in patent:Page/Page column 124

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