2-Bromopyridine → 3-Bromo-2,6-dimethylphenol

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]N=1.[CH3:8][CH2:9][CH2:10]CCCCCCCN.C(=O)([O-])[O-:20].[Cs+].[Cs+]>C1COCC1>[Br:1][C:2]1[C:9]([CH3:8])=[C:10]([OH:20])[C:5]([CH3:4])=[CH:6][CH:7]=1

Participants

Procedure

For example, bromo pyridine (Apollo) 11.6 is treated with amine 10.7 in the presence of cesium carbonate in THF or alternative solvent at reflux to give the amine 11.7. The amine is then converted to the sulfonyl chloride 11.9 through the intermediate chloride 11.8 as described in Scheme 10. Using the above procedures, but employing, in place of the amino alkyl phosphonate 10.7, different alkyl phosphonates 10.6, and in place of the pyridine 11.6 different halo pyridines 11.1, the corresponding products 6.3 are obtained.