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27011-89-8

Benzoic acid, 2-[(4-acetylphenyl)thio]- synthesis

1synthesis methods
-

Yield:27011-89-8 64%

Reaction Conditions:

with Cs2CO3 in dimethyl sulfoxide at 25; for 1 h;Inert atmosphere;UV-irradiation;

Steps:

2; 9 2-((4-Acetylphenyl)thio)benzoic acid (3j)

A 25 mL storage flask was charged with a stir bar, flame dried under vacuum and back filled with nitrogen three times.
The flask was then charged with Cs2CO3 (130.3 mg, 0.4 mmol, 2.0 eq.), 4'-Bromoacetophenone (39.8 mg, 0.2 mmol, 1.00 eq.), 2-mercaptobenzoic acid (46.2 mg, 0.3 mmol, 1.5 eq.) and 1.5 mL DMSO.
The reaction mixture was evacuated and purged with inert gas (N2) three times.
The reaction mixture was then placed into an LED-lined beaker and stirred with an air gas tube for cooling.
After stirred for 1 hour, the reaction mixture was washed with water, extracted with EtOA and concentrated in vacuum.
The product was isolated by flash chromatography (8:1 DCM:MeOH) as white solid (X=Br, 35 mg, 64%).
Physical State: white solid; Rf=0.3 (silica gel, 8:1 DCM:MeOH); 1H NMR (300 MHz, d6-DMSO) δ 7.99 (dt, J=8.7, 2.1 Hz, 2H), 7.92 (dd, J=7.8, 1.2 Hz, 1H), 7.56 (dt, J=8.4, 2.1 Hz, 2H, 2H), 7.46-7.40 (m, 1H), 7.32 (td, J=7.5, 1.2 Hz, 1H), 6.98 (dd, J=8.0, 0.9 Hz, 1H), 2.60 (s, 3H); 13C NMR (75 MHz, d6-DMSO) δ 197.7, 167.9, 140.3, 138.6, 136.7, 133.4, 132.9, 131.2, 130.6, 129.9, 129.6, 126.5, 27.2; HRMS (ESI-TOF): m/z calcd. for C15H12O3S ([M-H]+) 271.0429, found 271.0433.

References:

US2018/370911,2018,A1 Location in patent:Paragraph 0097; 0125; 0126