Phosphorus tribromide → 2-[4-(4-Bromomethylphenoxy)-phenyl]-3-(3,5-dimethoxyphenyl)-acrylic acid methyl ester

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Reaction Steps

A solution of PBr3 (4.8 mL of 1.0 M in CH2Cl2) was added dropwise to 12 (5.0 g, 11.9 mmol) dissolved in CH2Cl2 (20 mL) at temperature with good stirring. After 1 h, the solution was extracted with water (2×60 mL) and brine (20 mL). The organic phase was dried over anhydrous magnesium sulfate, filtered through a small bed of silica gel (20 g) and solvent was evaporated. The resulting tacky syrup was dried under high vacuum for 48 h at room temperature to yield the title compound (5.7 g, 99%): mp 79-81° C.; 1H NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.49 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 7.07 (d, J=8.4 Hz, 2H), 7.00 (d, J=8.4 Hz, 2H), 6.42 (t, J=2.4 Hz, 1H), 6.28 (d, J=2.0 Hz, 2H), 4.73 (d, J=4.8 Hz, 2H), 3.68 (s, 3H), 3.58 (s, 6H); Anal. (C25H23BrO5) C: calculated, 61.12; found, 62.26; H: calculated 4.80; found 4.88.

Provenance & Evidence