p-Toluenesulfonic acid → 4'-Bromo-2'-fluoro-4-propyl-2,3,4,5-tetrahydro-1,1'-biphenyl
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9]2)=[C:4]([F:18])[CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH:9]=2)=[C:4]([F:18])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A Dean-Stark condenser was attached, and a mixture of compound (68) (42.0 g, 133.2 mmol) and PTSA (0.42 g, 1 wt %) was refluxed in a toluene (300 mL) solvent for 3 hours. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and dried over magnesium sulfate. Toluene was distilled off by an evaporator, and thus 4′-bromo-2′-fluoro-4-propyl-2,3,4,5-tetrahydro-1,1′-biphenyl (69) (39.2 g, yield 99.0%) was obtained.