2,5-Difluoronitrobenzene → HCID 24890306, compound

HRID 1159348Notes

Reaction equation

HRID 1159348 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([SH:12])=[C:9]([OH:11])[CH:10]=1.CC(C)([O-])C.[K+].[F:21][C:22]1[CH:27]=[CH:26][C:25](F)=[CH:24][C:23]=1[N+]([O-])=O>>[F:21][C:22]1[CH:23]=[CH:24][C:25]2[S:12][C:8]3[C:9]([O:11][C:26]=2[CH:27]=1)=[CH:10][C:5]([O:4][CH2:3][C:2]([F:1])([F:13])[F:14])=[CH:6][CH:7]=3

Participants

4

Reactant 3

HCID 677672,5-DifluoronitrobenzeneHCID 23665647Potassium tert-butoxideHCID 57444205HCID 57444205, compound

Product 1

HCID 24890306HCID 24890306, compound

Procedure

3-Fluoro-7-(2,2,2-trifluoroethoxy)phenoxathiin can be prepared according to the teachings provided herein and the knowledge in the art. Briefly, treating 5-(2,2,2-trifluoroethoxy)-2-mercaptophenol with base followed by addition of 1,4-difluoro-2-nitrobenzene can afford 3-fluoro-7-(2,2,2-trifluoroethoxy)phenoxathiin. For example, 5-(2,2,2-trifluoroethoxy)-2-mercaptophenol can be combined with potassium tert-butoxide followed by combination with 1,4-difluoro-2-nitrobenzene which upon heating can afford 3-fluoro-7-(2,2,2-trifluoroethoxy)phenoxathiin. In an exemplary embodiment, the solvent used to dissolve potassium tert-butoxide and 1,4-difluoro-2-nitrobenzene can be anhydrous N,N-dimethylformamide. For example, 5-(2,2,2-trifluoroethoxy)-2-mercaptophenol dissolved in a THF/MTBE mixture can be added to potassium tert-butoxide in N,N-dimethylformamide; subsequent to their combination, under the conditions disclosed herein, the mixture can then be treated with 1,4-difluoro-2-nitrobenzene dissolved in N,N-dimethylformamide.

Workup

  1. temperatureupon heating can

Sources & evidence

ORD record
ord-50380c9d0b1f47f2be7ba0d36713df86
Source dataset
uspto-grants-2010_10
Patent number
US07812050B2

Reaction notes

Loading…