207680-98-6

Basic information

• Product Name: Benzonitrile, 4-[(4-fluorophenyl)hydroxymethyl]-3-(hydroxymethyl)-
• CAS NO: 207680-98-6
• Molecular Formula: C15H12FNO2
• Molecular Weight: 257.264
• Mol File: 207680-98-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-[(4-fluorophenyl)hydroxymethyl]-3-(hydroxymethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-[(4-fluorophenyl)hydroxymethyl]-3-(hydroxymethyl)-(207680-98-6)
• EPA Substance Registry System: Benzonitrile, 4-[(4-fluorophenyl)hydroxymethyl]-3-(hydroxymethyl)-(207680-98-6)

Safety Data

• Hazardous Substances Data: 207680-98-6(Hazardous Substances Data)

Upstream product

• 260371-16-2 4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile 
• 762266-07-9 4-(bis(4-fluorophenyl)hydroxymethyl)-3-(hydroxymethyl)benzonitrile 
• 82104-74-3 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile 
• 142-82-5 n-heptane 
• 352-13-6 4-flourophenylmagnesium bromide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 19070-16-7 3-(N,N-dimethylamino)propylmagnesium chloride 
• 7439-95-4 magnesium 

Downstream Products

• 64169-67-1 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 

Relevant articles and documents

CARBONYL ASYMMETRIC ALKYLATION

This invention relates to processes and intermediates for the stereoselective alkylation of carbonyl groups. The invention in particular allows the stereoselective preparation of the antidepressant drug escitalopram. It has been found that boric or boronic acid derivatives are useful bridging elements for the attachment of a chiral group to a compound containing a carbonyl group to be alkylated. The said borates and boronates are thus useful in a process for the asymmetric alkylation of a carbonyl group in a compound containing a carbonyl group and an anchor group capable of reacting with a boric or boronic acid derivative. The asymmetric alkylation can be carried out by admixing the compound containing a carbonyl group to be alkylated and the anchor group capable of reacting with a boric or boronic acid derivative with a boric or boronic acid derivative, adding a chiral alcohol, and adding an organometallic compound. After the alkylation reaction, the borate and boronate can be easily removed by hydrolysis.

PROCESS FOR THE PREPARATION OF A CYANO-ISOBENZOFURAN

A process for the preparation of citalopram and the pharmaceutically acceptable salts therof is disclosed by reacting 5-cyanophthalide with a 4-fluorophenyl magnesium halide, reducing the 3-hydroxymethyl-4-(4-fluoro-benzoyl)benzonitrile with an agent reducing ketones to alcohols, submitting the thus-obtained 3-hydroxymethyl-4- [(4-fluorophenyl)hydroxymethyl) benzonitrile to a cyclization reaction to give 1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile without 1,1-bis(4-fluorophenyl)-1,3-dihydro-5- isobenzofurancarbonitrile and treating 1,1-bis(4 fluorophenyl)-1,3-dihydro-5- isobenzofurancarbonitrile with a 3-(dimetylamino)propyl halide in the presence of a base.

Method for the preparation of citalopram

A method for the preparation of citalopram is described comprising reduction of the oxo group of a compound of formula (IV), wherein R1is CN, C1-6alkyloxycarbonyl or C1-6alkylaminocarbonyl, ring closure of the resulting hydroxy compound thereby obtaining the corresponding 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran, then if R1is cyano using it directly in the next step and if R1is C1-6alkyloxycarbonyl or C1-6alkylaminocarbonyl, conversion of the compound to the corresponding compound wherein R1is a cyano; and alkylation of the resulting 5-cyano compound with 3-dimethyl-aminopropylhalogenide in basic conditions thereby obtaining citalopram.