Potassium Carbonate → Isovanillin

Temperatur

85 °C

3-[5-(4-Amino-benzyl)-2-methoxy-phenoxy]-benzonitrile P-15. In an 8 mL vial equipped with a stir bar was placed (18) (250 mg, 0.798 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (192 mg, 0.878 mmol), potassium carbonate (331 mg, 2.39 mmol), 1,5-bis(diphenylphosphino)pentane (105 mg, 0.239 mmol), and dimethylformamide (4.5 mL). The mixture was degassed with nitrogen for 15 minutes and allylpalladium(II) chloride dimer (43.8 mg, 0.120 mmol) was added. The mixture was heated to 85° C. for 18 hours. The reaction mixture was filtered through celite and to the filtrate were added water (30 mL) and saturated ammonium chloride solution (30 mL). After extractions with ethyl acetate (2×75 mL), the organic portions were combined, washed with brine (50 mL), dried (MgSO4) and concentrated. The crude material was purified by silica gel column chromatography utilizing 50% ethyl acetate/hexanes to produce 118 mg (45% yield) of P-15 as a yellow viscous oil. MS (APCI+): 331.1 (M+1), LC-MS: >99%

1. customIn an 8 mL vial equipped with a stir bar
2. customThe mixture was degassed with nitrogen for 15 minutes
3. filtrationThe reaction mixture was filtered through celite and to the filtrate
4. additionwere added water (30 mL) and saturated ammonium chloride solution (30 mL)
5. extractionAfter extractions with ethyl acetate (2×75 mL)
6. washwashed with brine (50 mL)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customThe crude material was purified by silica gel column chromatography

ORD-Eintrag

ord-9216d16aa2c14bb38a1ce62562d51fc7

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08877816B2