2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester synthesis

9synthesis methods

Product Name:2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester
CAS Number:478375-37-0
Molecular formula:C15H21BO5
Molecular Weight:292.14

7120-41-4 Synthesis

7120-41-4
69 suppliers
$45.00/100mg

73183-34-3
568 suppliers
$6.00/5g

2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester

478375-37-0
23 suppliers
inquiry

Yield:478375-37-0 88.3%

Reaction Conditions:

with potassium acetate in Petroleum ether;

Steps:

158.2 Step 2:

Step 2:
Methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
A mixture of methyl 5-bromo-2-methoxybenzoate (2.09 g, 8.53 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (3.10 g, 12.2 mmol), potassium acetate (2.59 g, 26.4 mmol) and 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (600 mg, 0.820 mmol) in 1,4-dioxane (40 mL) was stirred at 80° C. for 2.5 h under nitrogen atmosphere.
The reaction mixture was filtered and the filtrate was evaporated in vacuo.
The residue was purified via flash chromatography on silica gel (solvent gradient: 0-10% ethyl acetate in petroleum ether) to yield 2.20 g (88.3%) of the title compound as a yellow solid. ¹H NMR (300 MHz, CDCl₃) δ 8.23 (s, 1H), 7.91 (d, J=8.4 Hz, 1H), 6.98 (d, J=8.4 Hz, 1H), 3.94 (s, 3H), 3.89 (s, 3H), 1.35 (s, 12H).

References:

US2018/65983,2018,A1