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p-Fluoronitrobenzene → 2-[4-(4-Nitrophenoxy)phenyl]oxazole

HRID 630318
Notes
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Reaction equation

HRID 630318 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.CC(C)([O-])C.[K+].F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.[OH-].[Na+]>CS(C)=O>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([O:12][C:9]2[CH:10]=[CH:11][C:6]([C:2]3[O:1][CH:5]=[CH:4][N:3]=3)=[CH:7][CH:8]=2)=[CH:21][CH:22]=1)([O-:28])=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 14798Sodium HydroxideHCID 23665647Potassium tert-butoxideHCID 1356214594-(Oxazol-2-yl)phenol

Product 1

HCID 684907472-[4-(4-Nitrophenoxy)phenyl]oxazoleYield 82.2%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Procedure

A solution of 4-(2-oxazolyl)phenol (10.8 g, 11.2 mmol) in DMSO (9 mL) was stirred as potassium tert-butoxide (1.5 g, 13.4 mmol) and 4-fluoro-nitrobenzene (1.3 mL, 12.3 mmol) were added sequentially. The reaction was stirred for 17 hours at ambient temperature. The reaction was poured into a cold aqueous sodium hydroxide solution (1 N). The solid was isolated by filtration to give 2.6 g of 2-[4-(4-nitrophenoxy)phenyl]oxazole.

Workup

  1. additionwere added sequentially
  2. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-5e9c295d09134aa79c8a967abcab7821
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09315509B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes