[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([S:10]C#N)[CH:7]=[CH:6][C:5]=1[OH:13].[CH3:14][C:15]1[CH:16]=[C:17]([S:26]CC2SC(C3C=CC(C(F)(F)F)=CC=3)=NC=2C)[CH:18]=[CH:19][C:20]=1[O:21]CC(O)=O.Cl>O.CCOCC>[C:15]1([CH3:14])[C:20]([OH:21])=[CH:19][CH:18]=[C:17]([S:26][S:10][C:8]2[CH:9]=[C:4]([CH3:3])[C:5]([OH:13])=[CH:6][CH:7]=2)[CH:16]=1
To a stirred solution of 33.0 g (825.6 mmol) NaOH in 200 ml water was added 44.0 g (266.3 mmol) of 2-methyl-4-thiocyanato-phenol at 85° C. [Wei, Zhi-Liang; Kozikowski, Alan P., A Short and Efficient Synthesis of the Pharmacological Research Tool GW501516 for the Peroxisome Proliferator-Activated Receptor delta, Journal of Organic Chemistry (2003), 68(23), 9116-9118]. The temperature was raised to 95° C. and the mixture stirred over night. After cooling (10° C.), ether and 90 ml of aqueous conc. HCl were added. The water phase was extracted with ether (two times). The organic phase was washed with brine, dried (Na2SO4) and evaporated. The residue was dissolved in 300 ml of DMSO and heated for 2 h at 95° C. Subsequently, the solution was poured onto ice water and extracted with three 1 l portions of TBME. The organic layers were washed with 700 ml of water, dried (Na2SO4) and evaporated to give 42.1 g of the title compound.
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