1-(4-Fluorophenyl)-1,3-dihydro isobenzofuran-5-carbonitile Chemical Properties

Melting point:

95-97°C

Boiling point:

375°C

Density 

1.29

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Dichloromethane, Methanol (Slightly, Sonicated)

form 

Solid

color 

White to Light Yellow

CAS DataBase Reference

64169-67-1(CAS DataBase Reference)

Safety Information

HS Code 

2932.99.7000

1-(4-Fluorophenyl)-1,3-dihydro isobenzofuran-5-carbonitile Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

An intermediate in the synthesis of Citalopram.

Synthesis

GENERAL STEPS: A solution of 4-fluorophenylmagnesium bromide was prepared by reacting 153.33 g (0.876 mol) of 4-fluorobenzene bromide, 25.33 g (1.055 mol) of magnesium scrapings and 0.05 g of iodine in 300 mL of anhydrous tetrahydrofuran. This Grignard reagent solution was slowly added to a suspension of 100 g (0.628 mol) 5-cyanophthalide. The reaction was carried out in 1000 mL of dichloromethane and the temperature was maintained at -6 to -2°C. Upon completion of the reaction, post-processing was carried out as in Example 1 to give a thick semi-solid product. This semi-solid was ground with 500 mL of isopropanol (IPA) and cooled at 0-5 °C to give the solid product 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran (2b). The solid was collected by filtration and washed with cold 50 mL IPA. The yield of the product was 130-140 g and the HPLC purity was 99.32%.

References

[1] Patent: WO2004/20425, 2004, A1. Location in patent: Page 11
[2] Patent: WO2004/20425, 2004, A1. Location in patent: Page 13-14

1-(4-Fluorophenyl)-1,3-dihydro isobenzofuran-5-carbonitile(64169-67-1)Related Product Information

• 4-Cyanobenzoic acid
• Dihydromyrcenol
• Benzofuran
• Methyl 4-cyanobenzoate
• Sodium cyanoborohydride
• Phenyl benzonitrile
• Citalopram hydrobromide
• Escitalopram
• Citalopram hydrochloride
• Citalopram
• (R)-Citalopram Oxalate
• CITALOPRAM-D4
• (S)-(+)-CITALOPRAM-D4 OXALATE
• (R)-Desmethyl Citalopram Hydrochloride
• DIDESMETHYL CITALOPRAM-D4
• (R)-(-)-CITALOPRAM
• 1-(4-Fluorophenyl)-1,3-dihydro isobenzofuran-5-carbonitile
• Cyano