تفاعل #513489

معادلة التفاعل

(5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

4-chlorophenyl boronic acid

K2CO3

→

(4″-chloro-4-trifluoromethyl-[1,1′;3′,1″]terphenyl-5′-yl)-acetic acid methyl ester

المذيبات

DME

ظروف التفاعل

المعالجة

1. 1
   ترشيحfiltered
2. 2
   workup.ADDITIONdiluted with EtOAc
3. 3
   غسيلwashed with Na2CO3, dil HCl, brine
4. 4
   تجفيفdried (MgSO4)
5. 5
   أخرىevaporated under reduced pressure
6. 6
   أخرىto give an off white solid
7. 7
   أخرىThe residue was purified by flash column chromatography (EtOAc:petroleum ether), 1H NMR (CDCl3) δ 7.71 (s, 4H), 7.65-7.68 (m, 1H), 7.42 (d, 2H), 7.52-7.48 (m, 2H), 7.36 (d, 2H), 3.77 (s, 2H), 3.74 (s, 3H)

الإجراء التجريبي

A solution of (5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (100 mg, 0.2 mmol), 4-chlorophenyl boronic acid (41 mg, 0.24 mmol), K2CO3 (2 M solution in H2O, 220 μL, 0.4 mmol) in DME (2.0 mL) was heated to 80° C. in the presence of bis(tri-t-Butylphosphine) palladium (0) (cat) for 2 hrs. The mixture was cooled to room temperature filtered, diluted with EtOAc, washed with Na2CO3, dil HCl, brine, dried (MgSO4) and evaporated under reduced pressure to give an off white solid. The residue was purified by flash column chromatography (EtOAc:petroleum ether), 1H NMR (CDCl3) δ 7.71 (s, 4H), 7.65-7.68 (m, 1H), 7.42 (d, 2H), 7.52-7.48 (m, 2H), 7.36 (d, 2H), 3.77 (s, 2H), 3.74 (s, 3H)

المصدر