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CAS No. : | 286844-91-5 | MDL No. : | MFCD09701422 |
Formula : | C14H11F3O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 332.30 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; phosphoric acid; In n-heptane; water; dimethyl sulfoxide; acetonitrile; | EXAMPLE 4A 1-(methylsulfonyl)-4-(4'-(trifluoromethoxy)phenoxy)benzene A solution of 1-fluoro-4-(methylsulfonyl)benzene (2.2 kg), KOH (906.3 g), 4-(trifluoromethoxy)phenol (2.364 kg) and DMSO (4.4 L) was heated to 90 C. and stirred until HPLC showed <0.5% starting material remained (about 10 hours). HPLC conditions: Zorbax SB-C8 4.6 mm*25 cm; mobile phase was a gradient of 70% water with 0.1% H3PO4/30% acetonitrile to 10% water with 0.1% H3PO4/90% acetonitrile over 15 minutes at a flow rate of 1.5 mL/min, followed by a five minute hold at 10/90; UV detection at 220 nM. Retention times: starting sulfone, 4.5 min; desired product, 7.8 min. The reaction mixture was cooled to room temperature, diluted with water (8.8 kg), and extracted with two portions of toluene (24 L and 4.7 L). The combined extracts were washed with 1N NaOH solution (11 kg) and water (2*11 kg), filtered, concentrated to a volume of approximately 6 L, treated with heptane (22 L) with agitation, stirred for 2 hours, and cooled to 0-5 C. until the mother liquor was assayed for the desired product at <5 mg/mL. The precipitate was filtered, washed with heptane (6.6 L) and dried under vacuum (100 mm Hg with nitrogen sweep) at 40 C. to provide 2.0 kg (96.4% wt potency, 89.6% yield) of the desired product. Recrystallization from methanol/water (4:8 v/v) gave the purified product with 98% recovery. 1H NMR (300 MHz, CDCl3) delta 7.9 (d, 2H), 7.3 (br d, 2H), 7.1 (d, 4H), 3.1 (s, 3H). | |
With potassium hydroxide; phosphoric acid; In n-heptane; water; dimethyl sulfoxide; acetonitrile; | EXAMPLE 1 1-(methylsulfonyl)-4-[4'-(trifluoromethoxy)phenoxy]benzene A solution of 1-fluoro-4-(methylsulfonyl)benzene (2.2 kg), KOH (906.3 g), 4-(trifluoromethoxy)phenol (2.364 kg) and DMSO (4.4 L) was heated to 90 C. and stirred until HPLC showed <0.5% starting material remained (about 10 hours). HPLC conditions: Zorbax SB-C8 4.6 mm*25 cm; mobile phase was a gradient of 70% water with 0.1% H3PO4/30% acetonitrile to 10% water with 0.1% H3PO4/90% acetonitrile over 15 minutes at a flow rate of 1.5 mL/min, followed by a five minute hold at 10/90; UV detection at 220 nM. Retention times: starting sulfone, 4.5 min; desired product, 7.8 min. The reaction mixture was cooled to room temperature, diluted with water (8.8 kg), and extracted with two portions of toluene (24 L and 4.7 L). The combined extracts were washed with 1N NaOH solution (11 kg) and water (2*11 kg), filtered, concentrated to a volume of approximately 6 L, treated with heptane (22 L) with agitation, stirred for 2 hours, and cooled to 0-5 C. until the mother liquor was assayed for the desired product at <5 mg/ML. The precipitate was filtered, washed with heptane (6.6 L) and dried under vacuum (100 mm Hg with nitrogen sweep) at 40 C. to provide 2.0 kg (96.4% wt potency, 89.6% yield) of the desired product. Recrystallization from methanol/water (4:8 v/v) gave the purified product with 98% recovery. 1H NMR (300 MHz, CDCl3) delta 7.9 (d, 2H), 7.3 (br d, 2H), 7.1 (d, 4H), 3.1 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-(methylsulfonyl)-4-(4'-(trifluoromethoxy)phenoxy)benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 3-(4-(methoxycarbonyl)phenyl)propanoic acid methyl ester In tetrahydrofuran; hexane at -78℃; for 3h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
278 hydroxy{3-hydroxy-2,2-dimethyl-1-[({4-[4-(trifluoromethoxy)phenoxy]phenyl}sulfonyl)methyl]propyl}formamide EXAMPLE 278 hydroxy{3-hydroxy-2,2-dimethyl-1-[({4-[4-(trifluoromethoxy)phenoxy]phenyl}sulfonyl)methyl]propyl}formamide Methyl 3-tertButyldimethylsilyloxy-2,2-dimethyl-propionate was converted to the title compound following the procedures of Examples 126A, substituting 4-(4'-trifluoromethoxyphenyloxy)-phenyl methyl sulfone for 4-(4'-trifluoromethylphenyl)-phenyl methyl sulfone, 126B, 75B, 75C, 213B and 125B. mp 112.5-113.5° C. 1H-NMR (300 MHz, DMSO-d6) δ 0.76 (s, 6H), 3.03-3.16 (m, 2H), 3.50-3.75 (m, 2H), 3.88 (d, 0.7H, J=9.0 Hz), 4.45 (d, 0.3H, J=9.0 Hz), 7.20-7.32 (m, 4H), 7.47 (d, 2H, J=9.0 Hz), 7.68 (s, 0.7H), 7.80 (m, 2H), 8.09 (s, 0.3H) MS (ESI, +Q1MS) 478 (M+H), 495 (M+NH4) Anal. Calcd for C20H22F3NO7S: C, 50.31; H, 4.64; N, 2.93. Found: C, 50.29; H, 4.68; N, 2.76. |