2241720-34-1 | Quinazoline, 7-bromo-2,4-dichloro-8-fluoro-6-iodo-

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$41.00	$29.00
250mg	95%	in stock	$47.00	$33.00
1g	95%	in stock	$71.00	$50.00
5g	≥97%	in stock	$279.00	$195.00

Description

• Catalog Number: BG12171
• Chemical Name: Quinazoline, 7-bromo-2,4-dichloro-8-fluoro-6-iodo-
• CAS Number: 2241720-34-1
• Molecular Formula: C8HBrCl2FIN2
• Molecular Weight: 421.8198
• MDL Number: MFCD32879380
• SMILES: Clc1nc(Cl)c2c(n1)c(F)c(c(c2)I)Br

Upstream Synthesis Route

To synthesize 7-bromo-2,4-dichloro-8-fluoro-6-iodoquinazoline, one could start from a simple quinazoline scaffold and sequentially introduce the halogen substituents through halogenation reactions. The proposed upstream synthetic route is as follows:

1. Begin with the base molecule of quinazoline.
2. Introduce the bromine substituent at the 7-position via electrophilic aromatic substitution (EAS) using Br2 and an appropriate Lewis acid catalyst, such as FeBr3, ensuring conditions favor para-bromination relative to the built-in nitrogen functions.
3. Follow with dichlorination at the 2 and 4-positions. This might be achieved using excess Cl2 with a suitable catalyst like AlCl3 under controlled conditions to ensure the proper regioselective placement of the chlorine atoms.
4. The next step is to introduce the fluorine at the 8-position. This could be accomplished with a nucleophilic aromatic substitution (S_NAr) using an appropriate fluorinating agent, such as KF, under high temperature or with the help of a phase transfer catalyst, which can replace a suitable leaving group previously introduced if direct fluorination of the quinazoline is not feasible.
5. Finally, to place the iodine atom at the 6-position, another EAS reaction can be carried out using I2 and an oxidizing agent such as HNO3 to convert the iodide to a more reactive iodonium species, or using ICl with an oxidant if direct iodination proves challenging.

Throughout these steps, one must purify intermediates to ensure regioselectivity and avoid over-halogenation. The actual experimental conditions such as solvents, temperature, and reaction time would require optimization for each step. Each transformation may require protection and deprotection strategies if the positions are sensitive to the reaction conditions applied in subsequent steps.