p-Fluoronitrobenzene → 1-Fluoro-2-(4-nitrophenoxy)benzene

HRID 1865091Notes

Reaction equation

HRID 1865091 reaction equation
CC[NH+](CCOC1C(C2ON=C(C)C=2)=CC=CC=1)CC.[Cl-].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.[F:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[OH:39]>>[F:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[O:39][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 97072-FluorophenolHCID 4090453824-20-7

Product 1

HCID 579749991-Fluoro-2-(4-nitrophenoxy)benzene

Procedure

Prepare the title compound in the manner analogous to the procedure set fourth in example E-221 using 4-fluoro-nitrobenzene and 2-fluorophenol (heat 2 hours at 60° C.). Purify the material by silica gel chromatography (Prep. 2000) eluting with methylene chloride/hexane 1:1 to provide the title compound as a yellow solid. Mass spectrum (m/e): 233.1 (M*). (Bruker 300) 1H NMR (CDCl3) 8.17-8.22 (2H, d), 7.14-7.28 (4H, m), 6.96-700 (2H, d).

Workup

  1. customPurify the material by silica gel chromatography (Prep. 2000)
  2. washeluting with methylene chloride/hexane 1:1

Sources & evidence

ORD record
ord-152aecbe351b4e608352a6452323b057
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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