p-Fluoronitrobenzene → 2-(4-Aminophenoxy)-5-ethyl-4-fluorophenol

HRID 1023959Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.C[O:12][C:13]1[CH:18]=[C:17]([CH2:19][CH3:20])[CH:16]=[CH:15][C:14]=1[OH:21].BrC1C([F:29])=CC(O)=C(OC)C=1>>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([O:21][C:14]2[CH:15]=[C:16]([F:29])[C:17]([CH2:19][CH3:20])=[CH:18][C:13]=2[OH:12])=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 9590p-Fluoronitrobenzene

HCID 624654-Ethylguaiacol

HCID 265965254-Bromo-5-fluoro-2-methoxyphenol

Product 1

HCID 591912892-(4-Aminophenoxy)-5-ethyl-4-fluorophenolYield 77%

Procedure

According to the procedure of example 20(a) except substituting 1-fluoro-4-nitro-2-(trifluoromethyl)benzene for 4-fluoronitrobenzene (210 μL; 2 mmol) and 2-methoxy-4-ethylphenol for 4-bromo-5-fluoro-2-methoxyphenol (444 mg; 2 mmol), the title compound (527 mg; 77%) was prepared as a light yellow solid after purification on silica gel (cyclohexane/ethyl acetate: 95/5).

Workup

customafter purification on silica gel (cyclohexane/ethyl acetate: 95/5)

Sources & evidence

ORD record: ord-ecda811d89a342fbbc4ee38f54bd7124
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722746B2

Reaction notes

Loading…