154264-95-6 | 7-Bromo-4-methyl-3,4-dihydro-2h-1,4-benzoxazine

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$12.00	$9.00
250mg	95%	in stock	$18.00	$13.00
5g	95%	in stock	$313.00	$219.00
25g	95%	in stock	$1,504.00	$1,053.00

Description

• Catalog Number: AE99462
• Chemical Name: 7-Bromo-4-methyl-3,4-dihydro-2h-1,4-benzoxazine
• CAS Number: 154264-95-6
• Molecular Formula: C9H10BrNO
• Molecular Weight: 228.0858
• MDL Number: MFCD02681913
• SMILES: Brc1ccc2c(c1)OCCN2C

Upstream Synthesis Route

To synthesize 7-Bromo-4-methyl-3,4-dihydro-2H-1,4-benzoxazine, the following upstream synthetic route can be proposed:

1. Start with the precursor ortho-vanillin (2-hydroxy-3-methoxybenzaldehyde), which provides the necessary aromatic ring structure for further functional group modifications.

2. Perform a methylation reaction on ortho-vanillin using methyl iodide in the presence of a base such as potassium carbonate, which methylates the phenolic -OH group to form 2-methoxy-3-methoxybenzaldehyde.

3. To introduce the bromine atom at the 7-position (para to methoxy group), treat the compound from step 2 with N-bromosuccinimide (NBS) in light or at elevated temperatures to achieve a radical bromination, giving 2-methoxy-3-methoxy-5-bromobenzaldehyde.

4. Engage in the formation of the 1,4-benzoxazine ring by reacting the aldehyde group with an appropriate amino alcohol under reductive amination conditions. Use 2-aminoethanol and a reducing agent like sodium cyanoborohydride to yield an intermediate amino alcohol with a secondary amine.

5. Finally, induce cyclization of the intermediate through acid-catalyzed dehydration, typically by using concentrated hydrochloric acid or sulfuric acid to form the 3,4-dihydro-2H-1,4-benzoxazine ring structure.

6. The protective methoxy group at the 2-position (ortho to the aldehyde function in the vanillin starting material) can be removed, if necessary, at the end of the synthesis or retained depending on the desired substitution pattern on the final product.

7. Once the dihydro-1,4-benzoxazine ring is formed, presume the existing 7-bromo and 4-methyl substitutions maintain their positions from previous steps. The product obtained is 7-Bromo-4-methyl-3,4-dihydro-2H-1,4-benzoxazine.