Phenol → 2-Bromo-6-phenoxypyridine

HRID 1588872Notes

Reaction equation

HRID 1588872 reaction equation
[O:1]([C:8]1[N:13]=[C:12](CO)[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.[Br:23]C1C=CC=C(Br)N=1>CS(C)=O>[Br:23][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:13]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 122742,6-DibromopyridineHCID 128791556-Phenoxy-2-pyridinemethanol

Product 1

HCID 8245892-Bromo-6-phenoxypyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 6-phenoxy-2-pyridinylmethanol may be prepared by first reacting phenol with 2,6-dibromopyridine in dimethyl sulfoxide under basic conditions to give 2-bromo-6-phenoxypyridine. This compound is then reacted at -70° C. with n-butyllithium in diethyl ether and then with dimethylformamide at -30° C. to give 2-formyl-6-phenoxypyridine. This aldehyde is in turn reacted with sodium borohydride in methanol, yielding the corresponding 6-phenoxy-2-pyridinylmethanol.

Sources & evidence

ORD record
ord-77d0eaf1f0104d8facd51eceb184f327
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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