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

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; R_f=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