Hydrochloric Acid → 2~5~-Methoxy[1~1~,2~1~:2~3~,3~1~-terphenyl]-2~2~-ol

温度

80 °C

To a stirred solution of phenylboronic acid (0.0842 g, 0.691 mmol), Ba(OH)2.8H2O (0.396 g, 1.26 mmol), and Pd(OAc)2 (0.0014 g, 0.00628 mmol) in DME:H2O (6:1, 7 mL) at room temperature was added 2,6-dibromo-4-methoxyphenol (0.0885 g, 0.314 mmol)). The mixture was then heated at 80° C. for 18 h. The reaction was 50% complete, and an additional 2.2 eq. of phenylboronic acid and 0.02 eq. Pd(OAc)2 were added and continued heating for another 24 h. At this point, the reaction was acidified to pH 1 with 1 N HCl and diluted with EtOAc (100 mL). The organic layer was washed with H2O (10 mL) and brine (10 mL) and then dried (MgSO4). After concentration, the residue was purified by flash chromatography (1 to 5% EtAOc/petroleum ether gradient) to afford the product (0.029 g, 33%) as a clear oil; 1H NMR (CDCl3) δ 3.83 (s, 3H), 5.04 (s, 1H), 6.86 (s, 2H), 7.37-7.42 (m, 2H), 7.45-7.50 (m, 4H), 7.54-7.68 (m, 4H); IR (film) 3540, 3060, 2930, 2820, 1605, 1580, 1500, 1470, 1425, 1360, 1330, 1210, 1175, 1120, 1060, 1040, 1025, 755, 700, and 500 cm−1; mass spectrum [EI], m/z 276 (M)+; Anal. Calcd. for C19H16O2.0.80H2O: C, 78.49; H, 6.10; N, 0.00, Found: C, 78.19; H, 5.54; N, 0.19.

1. temperaturecontinued heating for another 24 h
2. washThe organic layer was washed with H2O (10 mL) and brine (10 mL)
3. dry with materialdried (MgSO4)
4. concentrationAfter concentration
5. customthe residue was purified by flash chromatography (1 to 5% EtAOc/petroleum ether gradient)

ORDレコード

ord-35cf69dc0a55470a90556d7957062e46

出典データセット

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06451827B2