Sodium Hydroxide → HCID 9917169, compound

Participants

Reaction Conditions

Reaction Steps

At ambient temperature, to a stirred suspension of 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-isopropyl-phenol (0.306 g, 0.744 mmol) in 0.05 M Tris buffer pH 9: THF (10:3, 3.56 mL, 0.2 M) was added 2.5N NaOH (0.285 mL, 0.713 mmol) followed by a minimal amount of THF to form a solution. After 0.5 h, the reaction was cooled to 5° C. To the reaction was added dropwise, a solution of 4-chlorosulphonyl-2-hydroxybenzoic acid (0.338 g, 1.43 mmol) in THF (2.85 mL, 0.5M) while maintaining the pH at 10 with the simultaneous addition of 2N NaOH. After the addition was completed, the reaction was allowed to warm to ambient temperature and stirred for 1.5 h. At 5° C. additional 4-chlorosulphonyl-2-hydroxybenzoic acid (0.338 g, 1.43 mmol) in THF (2.85 mL, 0.5 M) was added in the exact same manner as above and the reaction was stirred for 1.5 h. The reaction was quenched with 2N HCl (40 mL) and extracted with EtOAc. The combined organic extracts were washed with 2N HCl (3×), dried (MgSO4) and concentrated. Purification on 2% H3PO4 /MeOH treated Biotage KP-Sil eluting with a 15 & 25% EtOAc/Hexane step gradient gave 0.294 g, (66%) of the title compound as a yellow solid, mp >225° C.; 1H NMR (DMSO-d6): δ 0.96 (d, 3 H), 1.02 (d, 3 H), 1.48 (s, 3 H), 2.50 (s, 3 H), 3.08 (heptet, 1 H), 7.26-7.39 (m, 5 H), 7.43 (dd, 1 H), 7.50 (t, 1 H), 7.66 (t, 1 H), 8.05 (d, 1 H), 8.21 (d, 1 H). IR (KBr) 3425, 2950, 1675, 1400 and 1190 cm-1. mass spectrum (-ESI), m/z 623/625 (M-H). Anal. Calcd. for C30H25BrO6S2 : C, 57.60; H, 4.03; N, 0.00. Found: C, 57.88; H, 4.29 N, 0.09.

Provenance & Evidence