52723-82-7 | 4-Bromo-5-fluoro-2-methylaniline

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$7.00	$5.00
5g	97%	in stock	$18.00	$12.00
10g	97%	in stock	$20.00	$14.00
25g	97%	in stock	$40.00	$28.00
100g	97%	in stock	$148.00	$103.00

Description

• Catalog Number: AB66945
• Chemical Name: 4-Bromo-5-fluoro-2-methylaniline
• CAS Number: 52723-82-7
• Molecular Formula: C7H7BrFN
• Molecular Weight: 204.03958319999998
• MDL Number: MFCD04973753
• SMILES: Nc1cc(F)c(cc1C)Br

Computed Properties

• Complexity: 120
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• XLogP3: 2.4

Upstream Synthesis Route

Here is a plausible synthesis route for 4-Bromo-5-fluoro-2-methylaniline:

1. Start with the commercially available 3-Bromoanisole as the starting material.
2. Perform a selective ortho-lithiation using n-BuLi (n-Butyllithium) in the presence of a suitable ligand like TMEDA (Tetramethylethylenediamine) to direct the lithiation to the 2-position relative to the methoxy group.
3. Quench the resulting aryllithium intermediate with N,N-Dimethylformamide (DMF) to introduce the formyl group at the 2-position via a formylation reaction, yielding 2-Formyl-3-bromoanisole.
4. Carry out a Vilsmeier-Haack reaction on the aldehyde to convert it into 3-Bromo-4-fluorobenzaldehyde by using POCl3 (Phosphorus oxychloride) and DMF in the presence of fluoride ions.
5. Reduce the aldehyde group of 3-Bromo-4-fluorobenzaldehyde to the corresponding amine using a suitable reducing agent like NaBH4 (Sodium borohydride) or hydrogenation over a palladium catalyst to yield 3-Bromo-4-fluoroaniline.
6. Finally, perform a Sandmeyer reaction where the amino group of 3-Bromo-4-fluoroaniline is replaced by a methyl group using methyl iodide and copper(I) iodide (CuI) as a catalyst under appropriate conditions, to give 4-Bromo-5-fluoro-2-methylaniline.

This synthesis offers a general approach, but the conditions for each step need to be optimized for maximum yield and purity, including the choice of solvent, temperature, and reaction times. Safety protocols must also be strictly followed due to the hazardous nature of some reagents.