Methyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate synthesis
- Product Name:Methyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
- CAS Number:478375-42-7
- Molecular formula:C15H21BO4
- Molecular Weight:276.14
150529-73-0
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73183-34-3
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478375-42-7
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Yield:478375-42-7 100%
Reaction Conditions:
with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;potassium acetate in 1,4-dioxane at 85; for 4 h;Inert atmosphere;
Steps:
255.1 Step 1: Methyl 2-(3-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)phenyl)acetate
Step 1: Methyl 2-(3-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)phenyl)acetateA suspension of methyl 2-(3-bromophenyl)acetate (5.00 g, 21.8 mmol), bis(pinacolato)diboron (11.1 g, 43.7 mmol) and potassium acetate (6.43 g, 65.5 mmol) in dioxane (43.7 ml) was degassed with bubbling nitrogen. PdC12(dppf)-CH2C12 adduct (0.446 g, 0.546 mmol) was added, and the reaction was heated to 85 °C for 4 h. The reaction was diluted with ethyl acetate (30 mL) and filtered through Celite. The organiclayer was washed with brine, separated, and dried with sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (220 g column, gradient from 0% to 40% EtOAc/hexanes) to give the title compound (6.00 g, 100%) as a colorless oil. ‘H NMR (400MHz, CDC13) ? 7.74 (s, 1H), 7.72 (s, 1H), 7.40 (t, J=1.7 Hz, 1H), 7.38-7.33 (m, 1H), 3.70 (s, 3H), 3.65 (s, 2H), 1.36 (s, 12H); LCMS(M+H) = 277.3; HPLC RT = 0.99 mm (Column: BEH C18 2.1 x 50 mm; Mobile Phase A: Water with 0.05% TFA; Mobile Phase B: Acetonitrile with 0.05% TFA; Gradient: 2- 98% B over 1.6 mm; Flow: 0.8 mL/min).
References:
WO2015/100282,2015,A1 Location in patent:Page/Page column 279
73183-34-3
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147283-87-2
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478375-42-7
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1878-67-7
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478375-42-7
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621-37-4
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478375-42-7
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42058-59-3
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478375-42-7
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$67.00/250mg