Guaiacol → 4-Fluoro-1-(2-methoxyphenoxy)-2-nitrobenzene

HRID 2276125Notes

Reaction equation

HRID 2276125 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].F[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].[CH3:21][O:22][C:23]1[CH:37]=[CH:36][CH:35]=[CH:34][C:24]=1[O:25][C:26]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:27]=1[NH2:28].[NH2:38][C:39]1[S:40][CH:41]=[CH:42][N:43]=1>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1.[F:33][C:30]1[CH:31]=[CH:32][C:26]([O:25][C:24]2[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=2[O:22][CH3:21])=[C:27]([NH:28][C:4]([NH:38][C:39]2[S:40][CH:41]=[CH:42][N:43]=2)=[O:9])[CH:29]=1

Participants

6

Reactant 4

HCID 460GuaiacolHCID 21552-AminothiazoleHCID 677672,5-DifluoronitrobenzeneHCID 26189650HCID 26189650, compound2×

Product 2

HCID 59732906HCID 59732906, compoundYield 72%HCID 669990164-Fluoro-1-(2-methoxyphenoxy)-2-nitrobenzeneYield 81%

Procedure

5-Fluoro-2-(2-methoxyphenoxy)-1-nitrobenzene (1.07 g, 81%) was prepared from 2-methoxyphenol (0.62 g, 5.5 mmol) and 2,5-difluoro-1-nitrobenzene (0.8 g, 5.0 mmol) following the general procedure A. This compound was reduced to 2-(2-methoxyphenoxy)-5-fluoroaniline (0.58 g, 66%) following the general procedure B. 1-[5-Fluoro-2-(2-methoxyphenoxy)phenyl]-3-(thiazol-2-yl)urea (129 mg, 72%) was prepared from 5-fluoro-2-(2-methoxyphenoxy)aniline (117 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-fa99cd4a8ede4b579fbaa7cd8264bc55
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Reaction notes

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