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ChemicalBook CAS DataBase List Benzoic acid, 2-hydroxy-4-(methylthio)-
67127-67-7

Benzoic acid, 2-hydroxy-4-(methylthio)- synthesis

3synthesis methods
-

Yield:67127-67-7 93%

Reaction Conditions:

with boron tribromide in dichloromethane at -65; for 3 h;

Steps:

1.A A. 2-Hydroxy-4-(methylthio)benzoic acid

2-Methoxy-4-(methylthio)benzoic acid (1.002 g, 5.05mmol) was dissolved in dichloromethane (18 mL). Thesolution was cooled to -65 °C in a dry ice/chloroform bath.Then a dichloromethane solution of boron tribromide (5.4 mL,5.4 mmol) was added slowly. After 3 hours, the reaction wasquenched with water (5 mL) and 1 N HCl (10 mL). Afterstirring for 10 minutes, the reaction was extracted withdichloromethane '(100 mL). The organic layer was washed with1 N HC1 (10 mL) and then dried over magnesium sulfate,filtered, and concentrated to give the pure product as apale yellow solid (866 mg, 4.70 mmol, 93%).IR(CHC13): 1657, 1616, 1451, 1287, 1225, 918 cm"1.(400 MHz, DMSO-de): 8 7.63(d, J=8.0 Hz, 1H) ; 6.75(m,2H) ; 2.46(S,3H) .IS-MS, m/e 185.2 (m+1).Analysis for CgHgSC^ :Calcd: C, 52.16; H, 4.38;Found: C, 52.26; H, 4.40.

References:

WO2004/108677,2004,A1 Location in patent:Page 38-39