4-Nitrophenol → 1-Fluoro-4-[(4-nitrophenoxy)methyl]benzene

HRID 453936Notes

Reaction equation

HRID 453936 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromide

Product 1

HCID 9575111-Fluoro-4-[(4-nitrophenoxy)methyl]benzeneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-nitrophenol (1.39 g, 10 mmol), potassium carbonate (1.38 g, 10 mmol) and 4-fluorobenzyl bromide (1.89 g, 10 mmol) in 20 ml of anhydrous DMF was stirred at 100° C. for 2 days. After cooling to room temperature, the reaction mixture was poured into 200 ml of ice-water with stirring. The solid was filtered and washed with water and dried to give 2.37 g (96%) of 1-nitro-4-(4-fluorobenzyloxy)-benzene as yellow solids.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringwith stirring
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-3d95063bd2424e08b0fc0cdde57fefc8
Source dataset
uspto-grants-2013_07
Patent number
US08492588B2

Reaction notes

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