Reaktion #65797

Reaktionsgleichung

1-(2-bromocyclopenten-1-yl)-4-(methylthio)benzene

4-fluorophenylboronic acid

Na2CO3

→

1-[2-(4-fluorophenyl)cyclopenten-1-yl]-4-(methylthio)benzene

Lösungsmittel

toluene

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux overnight
2. 2
   Einengenconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
4. 4
   Waschenwashed with water
5. 5
   Trocknendried (MgSO4)
6. 6
   SonstigePurification by silica gel chromatography with hexane

Vorschrift

Under nitrogen, 1.5 g (5.6 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylthio)benzene (Step 2) was reacted with 1.5 g (11 mmol) of 4-fluorophenylboronic acid (Lancaster) in 30 mL of toluene, 20 mL of ethanol, and 25 mL of 2M Na2CO3 in the presence of 250 mg of Pd(PPh3)4. The reaction was vigorously stirred at reflux overnight and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water, dried (MgSO4), and reconcentrated. Purification by silica gel chromatography with hexane gave 1-[2-(4-fluorophenyl)cyclopenten-1-yl]-4-(methylthio)benzene (41 in Synthetic Scheme X when R5 =SCH3, R10 =F, and R1, R2, R3, R4, R6, R7, R8, R9, R11, and R12 =H) as a colorless solid. mp 46-47° C.; NMR (CDCl3) d 2.04 (m, J=7 Hz, 2H), 2.45 (s, 3H), 2.86, (t, J=7 Hz, 4H), 6.86-6.94 (m, 2H), 7.08 (br s, 4H), 7.10-7.18 (m, 2H).

Quelle