Pyrazole → 2-(1H-Pyrazol-1-yl)phenol

HRID 1581789Notes

Reaction equation

HRID 1581789 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1.B(Br)(Br)Br>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N:12]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[OH:2])[CH:16]=[CH:15][CH:14]=[N:13]1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 25134Boron tribromideHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 155683282-(1H-Pyrazol-1-yl)phenol

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Methoxyphenylboronic acid (2 eq.) and pyrazole (1 eq.) are coupled with copper(II) acetate catalysis as described in Tetrahedron Lett. 39:2941-44, 1998 and the product is demethylated by treatment with boron tribromide in dichloromethane (see, for example, Synth. Commun. 27(20):3581-90, 1997) to yield 2-(pyrazol-1-yl)phenol. This phenolic product is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to give the title epoxide.

Sources & evidence

ORD record
ord-70930e46ef1e4c8dbe898a603d2137eb
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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