4-Amino-3-fluorophenol → 5-Amino-2,4-difluorophenol

HRID 658453Notes

Reaction equation

HRID 658453 reaction equation
F[C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([F:11])[CH:5]=[CH:4][C:3]=1[OH:12].NC1C=CC(O)=CC=1[F:21]>>[F:21][C:4]1[CH:5]=[C:6]([F:11])[C:7]([NH2:8])=[CH:2][C:3]=1[OH:12]

Participants

3

Reactant 2

HCID 27359194-Amino-3-fluorophenolHCID 69761116HCID 69761116, compound

Product 1

HCID 27829995-Amino-2,4-difluorophenolYield 97%

Procedure

This compound was prepared from 2,4-difluoro-3-nitrophenol (2.35 g, 13.4 mmol) in the manner described for 4-amino-3-fluorophenol, affording 1.89 g (97%) of 2,4-difluoro-5-aminophenol as a tan solid. 1H-NMR (DMSO-d6) δ 9.26 (s, 1H), 6.89 (t, J=10.7 Hz, 1H), 6.33 (t, J=9.2 Hz, 1H), 4.82 (s, 2H).

Sources & evidence

ORD record
ord-73c062c4cc634780845aaa962bda2cf6
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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