1,2,4-Trifluoro-5-nitrobenzene → 4-Amino-2,5-difluorophenol

HRID 658459Notes

Reaction equation

HRID 658459 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([F:11])=[CH:4][C:3]=1F.NC1C(F)=CC([OH:21])=CC=1F>>[NH2:8][C:6]1[C:5]([F:11])=[CH:4][C:3]([OH:21])=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 750121,2,4-Trifluoro-5-nitrobenzeneHCID 27787614-Amino-3,5-difluorophenol

Product 1

HCID 27787624-Amino-2,5-difluorophenolYield 72.3%

Procedure

This compound was prepared from 1,2,4-trifluoro-5-nitrobenzene (5.0 g, 28 mmol) in the manner described for 4-amino-3,5-difluorophenol, affording 3.0 g (72.3%) of 4-amino-2,5-difluorophenol. 1H-NMR (DMSO-d6) δ 9.04 (s, 1H), 6.67 to 6.46 (m, 2H), 4.64 (s, 2H); MS GC-MS M+=146.1, RT=1.04 min.

Sources & evidence

ORD record
ord-beffefa8108c45c689635d96172d0fc0
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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