hydrogen bromide in water; toluene T=5 - 10°C; Heating / reflux;

1: With sulfuric acid in water T=100°C; 8 h; 2: With sodium hydroxide in water; toluene T=25 - 35°C; pH=8 - 8.5; 3: With hydrogen bromide in water; isopropyl alcohol T=0 - 20°C;

1: With sodium hydride in dimethyl sulfoxide T=25°C; 2.67 h; 2: With hydrogen bromide in water T=10°C; pH=7;

ammonium hydroxide; sulfuric acid; hydrogen bromide in water; acetone

1: 1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; 1-dimethylamino-3-chloropropane With sodium hydride in dimethyl sulfoxide; toluene T=20 - 25°C; 2.75 - 3.83333 h; 2: 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran-carbonitrile With hydrogen bromide in water; isopropyl alcohol; toluene pH=8 - 8.5; 13 h;

1: sodium hydride in paraffin oil (nujol); dimethyl sulfoxide T=60 - 65°C; Heating / reflux; 2: 1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; 1-dimethylamino-3-chloropropane With sodium methylsulfinylmethanide in water; dimethyl sulfoxide; toluene T=25 - 30°C; 2.75 - 3.83333 h; 3: 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran-carbonitrile With hydrogen bromide in water; isopropyl alcohol; toluene pH=8.5 - 9; 11 h;

1: With trichlorophosphate in pyridine T=5 - 115°C; 3 - 4 h; 2: With ammonia in water T=10°C; pH=9; 3: With hydrogen bromide in acetone T=10°C; pH=4 - 5;

in water; acetone pH=1;

1.1: iodine; magnesium / tetrahydrofuran / 5 h / 80 - 85 °C / Reflux 2.1: tetrahydrofuran / 0.25 h / -5 °C 2.2: 0.5 h / -5 - 20 °C 2.3: pH 2 3.1: sulfuric acid / water / 6 h / 70 °C 4.1: hydrogen bromide / isopropyl alcohol; acetic acid / 1 h / 20 - 70 °C / pH ~ 2 View Scheme

1.1: tetrahydrofuran / 0.25 h / -5 °C 1.2: 0.5 h / -5 - 20 °C 1.3: pH 2 2.1: sulfuric acid / water / 6 h / 70 °C 3.1: hydrogen bromide / isopropyl alcohol; acetic acid / 1 h / 20 - 70 °C / pH ~ 2 View Scheme