ChemicalBook CAS DataBase List 2-bromo-5-methyl-phenol

2-bromo-5-methyl-phenol synthesis

8synthesis methods

Product Name:2-bromo-5-methyl-phenol
CAS Number:14847-51-9
Molecular formula:C7H7BrO
Molecular Weight:187.03

2-bromo-5-methyl-phenol can be synthesized through several methods. One common method involves the bromination of 5-methylphenol (m-cresol) using bromine in the presence of a catalyst such as iron powder. The reaction typically occurs under controlled temperature conditions to ensure selective bromination at the desired position.

2835-98-5 Synthesis

2835-98-5
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14847-51-9
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$9.00/100mg

Yield:14847-51-9 20%

Reaction Conditions:

with hydrogen bromide;sodium nitrite;copper(I) bromide in water;ethyl acetate;

Steps:

233.A A.

A. 2-Bromo-5-methylphenol A solution of sodium nitrite (2.8 g, 41 mmol) in 5 ml water was added rapidly with stirring to an ice-cooled mixture of 6-amino-m-cresol (5.0 g, 41 mmol) and 48% hydrobromic acid (17 ml, 100 mmol). The temperature was kept below 10° C. by addition of ice chips. The diazonium salt solution was then added in portions over a period of 30 min to a boiling mixture of copper(I) bromide (6.4 g, 22 mmol) and 48% hydrobromic acid (5 ml). The resulting mixture was refluxed for an additional 30 min, then was cooled and extracted with ether (2*100 ml). The combined organic extracts were washed with water, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel using 98:2 hexanes/ethyl acetate to afford 233A (1.6 g, 20%) as an oil.

References:

US2002/143024,2002,A1 US6638937,2003,B2