ChemicalBook CAS DataBase List 4-Difluoromethoxyphenylboronic acid pinacol ester

4-Difluoromethoxyphenylboronic acid pinacol ester synthesis

6synthesis methods

Product Name:4-Difluoromethoxyphenylboronic acid pinacol ester
CAS Number:887757-48-4
Molecular formula:C13H17BF2O3
Molecular Weight:270.08

5905-69-1
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$10.00/5g

73183-34-3
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$6.00/5g

4-Difluoromethoxyphenylboronic acid pinacol ester

887757-48-4
74 suppliers
$22.00/100mg

Yield:887757-48-4 74%

Reaction Conditions:

with potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ in N,N-dimethyl-formamide at 90; for 1 h;Inert atmosphere;

Steps:

13.B-9.A

A. 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolaneA mixture of commercially available l-bromo-4-(difluoromethoxy)benzene (1 g, 4.48 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1.2g, 4.71 mmol), potassium acetate (1.3 g, 13.4 mmol), and PdCl₂(dppf)-CH₂Cl₂ Adduct (0.18 g, 0.22 mmol) in DMF (15 mL) was stirred under nitrogen at 90 ⁰C for 1 hour. Diluted with DCM, washed with water, sat. NaHCC^, brine, dried (MgSC^), and concentrated.The crude was purified using ISCO flash chromatography (silica gel/ hexanes/ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4- (difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane 13A (1.12 g, 3.32 mmol, 74.0 % yield) as a brown oil.

References:

WO2010/104830,2010,A1 Location in patent:Page/Page column 98-99