4-Amino-3-fluorophenol → 4-Amino-3-(methylsulfanyl)phenol

HRID 658465Notes

Reaction equation

HRID 658465 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.NC1C=CC(O)=CC=1F>>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([OH:12])=[CH:4][C:3]=1[S:2][CH3:1]

Participants

3

Reactant 2

HCID 27359194-Amino-3-fluorophenolHCID 441857023-(Methylthio)-4-nitrophenol

Product 1

HCID 190483494-Amino-3-(methylsulfanyl)phenolYield 81.3%

Procedure

This compound was prepared from 3-(Methylsulfanyl)4-nitrophenol (3.2 g, 17.3 mmol) in the manner described for 4-amino-3-fluorophenol, affording 2.18 g (81.3%) of the title compound. 1H-NMR (DMSO-d6) δ 8.56 (s, 1H), 6.60 (d, J=2.7 Hz, 1H), 6.53 (d, J=8.7 Hz, 1H), 6.43 (dd, J=8.7, 2.4 Hz, 1H), 2.28 (s, 3H).

Sources & evidence

ORD record
ord-39205e5895124b97bbb2f1897730a49b
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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