4-(Methylsulfonyl)phenol

4-(Methylsulfonyl)phenol is a reagent in the synthesis of pyrazolo[3,4-d]pyrimidine derivatives as GPR119 agonists. Also a reagent in the synthesis of novel 2-(pyridine-2-yl)-1H-benzimidazole derivatives as potent glucokinase activators.

Step 2. 4-(methylsulfonyl)phenol Oxone (0.99 g, 6.5 mmol) (Aldrich cat22803-6) was added in portions to a solution of 4-(methylthio)phenol (0.50 g, 3.2 mmol) in ethanol (10.0 mL) and water (10.0 mL) at room temperature. The reaction mixture was stirred for 18 h then partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford 4-(methylsulfonyl)phenol as a semisolid (0.60 g, 96percent). LCMS calculated for C7H9O3S (M+H)Reference Example 4 a) 4-Methanesulfinyl-phenol : H2WO4 (0. 029 g, 0.114 mmol) was stirred in H20 (10 ml). 50percent NaOH (0.040 ml) was first added (pH>12) and then AcOH (0.040 ml) to reach pH 5. 4-methylsulfanyl- phenol (4 g, 0.029 mol) was added and the reaction mixture was heated to 65 °C. 30percent H202 in H20 (3 mi) was added in portions over 10 minutes. The reaction mixture was allowed to stir at room temperature for 1 h. 50percent NaHS03 was added to quench the reaction. Methylene chloride was added and the compound was washed with brine and purified by chromatography (0 o 10 percent EtOH in methylene chloride) to give 1.9 g of 4-methanesulfinyl-phenol (1) (42percent) and 1.5 g of 4-methanesulfonyl-phenol (2) (30percent).General procedure: To a 0.25 M water(3.0 mL) solution of PPTS I (2.5 mol percent) and sulfide 1a, H2O2 (35percent v/v in water1.1 equiv) was added. The resulting mixture was stirred at room temperatureand followed by GC–MS until completion (2a/3a ratio 98:2, 95percent conversion).The reaction mixture was filtered and extracted with CH2Cl2. The combinedorganic phase was dried on Na2SO4 and concentrated under reduced pressure.Pure sulfoxide 2a was obtained by flash column chromatography (silica gel, 70:30 hexane/EtOAc) in 87percent yield. 1H NMR (500 MHz, CDCl3) d: 7.66–7.63 (m, 2H), 7.54–7.50 (m, 3 H), 2.72 (s, 3H); 13C NMR (125 MHz, CDCl3) d: 145.8, 131.0, 129.3, 123.5, 44.0.17a

Molecular Weight:172.20
XLogP3:0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:172.01941529
Monoisotopic Mass:172.01941529
Topological Polar Surface Area:62.8
Heavy Atom Count:11
Complexity:206
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes