I would like to use each of the two compounds separately in a synthetic procedure, but none of them is commercially available. 2-hydroxy-4-methoxylbenzaldehyde is commercially available and its Friedel Craft's bromination would give a mixture of the two compounds.
If both or either of them is a solid, you could try to crystallize out selectively.
try to transforme them into semicarbazones then separate using fractionnal cristallisation or column chromatography.
You can use column chromatography. Using an isocratic system
Check TLC with different solvent systems to see the separation of the two compounds to find out whether you can separate them by column chromatography!
Thank you colleagues for your responses. Considering their structures they are expected to have same polarity, so TLC and column chromatography may not be effective. Since they are both solids at room temperature, fractional crystallisation may be more effective.
Spot the mixture on a TLC plate to see how many components it contains. If it gives two components that are well resolved then, you can separate both using a column chromatography. A short column will do. Secondly, if u can access a GC, u can run the sample and see the components it gives with their retention time then, u would know if a column is best used for the separation.
Prep HPLC is also a better method to separate both compounds if u can access it.
By using the HPTLC (High Performance thin layer chromatography) followed by column chromatography you can separate the reaction mixture.
Because the phenol is the most polar group, and is sterically blocked by an ortho bromine, the isomers should separate well upon ordinary silica gel chromatography. You can quickly find out by TLC of a test reaction mixture.
If you need large quantities, the smaller amounts isolated by chromatography can be used to seed fractional recrystallizations.
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