1215860-20-0 | Methyl 5-bromo-6-methylpicolinate

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$50.00	$35.00
5g	98%	in stock	$241.00	$169.00
10g	98%	in stock	$448.00	$314.00
25g	98%	in stock	$882.00	$618.00
100g	98%	in stock	$3,089.00	$2,162.00

Description

• Catalog Number: AA53374
• Chemical Name: Methyl 5-bromo-6-methylpicolinate
• CAS Number: 1215860-20-0
• Molecular Formula: C8H8BrNO2
• Molecular Weight: 230.0586
• MDL Number: MFCD09753045
• SMILES: Cc1nc(ccc1Br)C(=O)OC

Upstream Synthesis Route

To synthesize Methyl 5-bromo-6-methylpicolinate, one would likely start with 6-methylpicolinic acid as the precursor. Here is a streamlined synthesis route:

1. Begin with 6-methylpicolinic acid as the starting material.
2. Protect the carboxylic acid group by converting the 6-methylpicolinic acid into its corresponding acid chloride using thionyl chloride (SOCl2), followed by esterification with methanol to form methyl 6-methylpicolinate.
3. Introduce the bromo substituent at the 5-position using 5-bromination through a directed lithiation technique where n-BuLi (n-butyllithium) is used to form the lithium derivative at the position meta to the nitrogens directed by the ester group. Then, bromine (Br2) is added to accomplish halogenation.
4. Isolate and purify the resulting Methyl 5-bromo-6-methylpicolinate using standard separation and purification techniques such as column chromatography followed by recrystallization to obtain the final product with a high degree of purity.

It is critical to control the reaction conditions and stoichiometry to prevent over-bromination and other potential side reactions. The choice of solvents, temperature control, and reaction times are key factors to optimize for successful synthesis.