111043-09-5 | 1-(3-Bromopyridin-2-yl)ethanone

Packsize	Purity	Availability	Price	Discounted Price
250mg	95%	in stock	$10.00	$7.00
1g	95%	in stock	$18.00	$13.00
5g	95%	in stock	$26.00	$18.00

Description

• Catalog Number: AD76887
• Chemical Name: 1-(3-Bromopyridin-2-yl)ethanone
• CAS Number: 111043-09-5
• Molecular Formula: C7H6BrNO
• Molecular Weight: 200.0326
• MDL Number: MFCD18257141
• SMILES: CC(=O)c1ncccc1Br

Computed Properties

• Complexity: 138
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• XLogP3: 1.6

Upstream Synthesis Route

The synthesis of 1-(3-Bromopyridin-2-yl)ethanone can be approached from 2-bromopyridine as the starting material. Here is a concise upstream pathway:

1. **Acetylation**: React 2-bromopyridine with acetic anhydride in the presence of a suitable base, such as triethylamine or pyridine, to introduce the ethanone group through acetylation at the methyl position. The base is used to neutralize the acetic acid formed during the reaction and to act as a catalyst.

2. **Halogen exchange (if starting from 2-chloropyridine)**: If beginning with 2-chloropyridine instead, perform a halogen exchange using a brominating agent like N-bromosuccinimide (NBS) with a radical initiator such as AIBN (azobisisobutyronitrile) under irradiation or heating to switch the chlorine atom to a bromine atom, giving 2-bromopyridine.

3. **Positional selective bromination**: To introduce the bromine at the 3-position of the pyridine ring if not already substituted, conduct a bromination with Br2 in the presence of a catalyst or directing group that promotes electrophilic bromination at the desired position. A Lewis acid, such as iron(III) bromide, can be used for this transformation.

Each step may require optimization of reaction conditions, temperature control, and purification steps including column chromatography or recrystallization to achieve desired quality and yield of the product, 1-(3-Bromopyridin-2-yl)ethanone. The entire synthesis should be conducted under inert atmosphere, using anhydrous solvents to prevent byproduct formation and ensure high selectivity.