2-[4-(4-fluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesis
- Product Name:2-[4-(4-fluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- CAS Number:1355052-34-4
- Molecular formula:C18H20BFO3
- Molecular Weight:314.16
886762-45-4
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Yield:1355052-34-4 90%
Reaction Conditions:
with potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 in 1,4-dioxane at 90; for 18 h;Product distribution / selectivity;Inert atmosphere;
Steps:
4.B
Method B: To a suspension of compound 3 (10 g, 31.8 mmol) in dioxane(320 mL) was added Pd(dppf)Cl2'CH2Cl2 (0.82 g, 1.0 mmol) and reaction mixture was degassed by repeating argon/vacuum cycles. The suspension was stirred for 10 min at room temperature, bis(pinacolato)diboron (8.9 g, 35.0 mmol) and potassium acetate (0.97 g, 95.4 mmol) were added, and the reaction mixture was heated at 90°C for 18 h under argon. Upon cooling to room temperature, the mixture was filtered through a pad of celite and concentrated under reduced pressure. The residue was purified by automated column chromatography on silica gel using a CombiFlash system (5% ethyl acetate in hexanes) to give compound 4 as a pale brown solid (9.0 g, 90% yield, Rf = 0.4, eluent (10% ethyl acetate in hexanes), LC/MS: m/z= 315 [M+H]+, 1H NMR (400 MHz, CD3C1): δ 7.67 (d, J = 8.6 Hz, 2H), 7.06-6.96 (m, 4H), 6.93 (d, J = 8.6 Hz, 2H), 1.33 (s, 12H)).
References:
WO2012/7836,2012,A1 Location in patent:Page/Page column 83-84
1765-93-1
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55102-99-3
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371-41-5
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350-46-9
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