1,2,3-Trifluoro-4-nitrobenzene → 4-Amino-2,3-difluorophenol

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([F:11])[C:3]=1[F:12].NC1C(F)=CC([OH:21])=CC=1F>>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:21])=[C:3]([F:12])[C:4]=1[F:11]

Participants

Reactant 2

HCID 698711,2,3-Trifluoro-4-nitrobenzene

HCID 27787614-Amino-3,5-difluorophenol

Product 1

HCID 27787664-Amino-2,3-difluorophenolYield 84%

Procedure

This compound was prepared from 1,2,3-trifluoro-4-nitrobenzene (5.0 g, 28 mmol) in the manner described for 4-amino-3,5-difluorophenol, affording 0.60 g (84%) of 4-amino-2,3-difluorophenol. 1H-NMR (DMSO-d6) δ 9.19 (s, 1H), 6.59 to 6.53 (m, 1H), 6.48 to 6.41 (m, 1H), 4.85 (s, 2H); TLC (12% DCM/Hex), Rf=0.08.

Sources & evidence

ORD record: ord-3a5793a63d1345cba0beb0e0311fd238
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076488B2

Reaction notes

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