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

HRID 1993100Notes

Reaction equation

HRID 1993100 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

5

Reactant 3

HCID 79732-BromopyridineHCID 8916DecylamineHCID 10796Cesium carbonate

Product 1

HCID 126735113-Bromo-2,6-dimethylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Sources & evidence

ORD record
ord-e3c22f2f97ff4bcaa09756e46c1b834b
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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