Bromine → (S)-2-[4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-3-phenyl-propionic acid

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Prepared from 4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenol (Example 41) and (R)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 97). White solid: [a]D25=+17.94° (10.30 mg/mL CHCl3): NMR (CDCl3); δ8.31 (ddd, J=8, 1, 1 Hz, 1 H), 7.76 (ddd., J=8, 1, 1 Hz, 1 H), 7.60 (ddd, J=8, 8, 1 Hz, 1 H), 7.54 (d, J=8 Hz, 1 H), 7.44-7.29 (m, 6 H), 7.24-7.20 (m, 4 H), 7.19-7.04 (m, 3 H), 6.62 (d, J=8 Hz, 1 H), 5.08 (dd, J=7, 5 Hz, 1 H), 3.44 (d, J=5 Hz, 1 H), 3.43 (d, J=7 Hz, 1 H); MS (FAB+): [M+H], bromine isotope pattern, 553 (11%), 569 (12%); Anal. Calc. for C31H21BrO3S: C, 67.27, H, 3.82, N, 0.00. Found: C, 65.17, H, 3.64, N, 0.04. Analytical HPLC determined that this compound was 98.9% pure [column:novapak, 5 micron (4.6 ×250 mm); isocratic, 7:3 accetonitrile: 0.01 M potassium dihydrogen phosphate, pH =3.5; flow rate =1.0 mL/min].

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