p-Fluoronitrobenzene → HCID 22663619, compound

HRID 392387Notes

Reaction equation

HRID 392387 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1>CN(C)C=O.ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 804592-Benzyloxyphenol

Product 1

HCID 22663619HCID 22663619, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-benzyloxyphenol (6.01 g, 30 mmol) in anhydrous N,N-dimethylformamide (25 mL) was treated with anhydrous potassium carbonate (7.6 g, 55 mmol), then with 4-fluoronitrobenzene (3.53 g, 25 mmol), and heated to 90° C. for 5 h under nitrogen. The solution was cooled to room temperature, diluted with dichloromethane (50 mL), and treated with DOWEX® 550A OH anion exchange resin (10 g) which had been washed dry with methanol. The mixture was stirred for 3 h, filtered, and the filtrate concentrated in vacuo (exhaustively at end to remove DMF). The residue was chromatographed on silica gel (eluted with 2:1 hexane/ethyl acetate) to afford 4-(2-benzyloxyphenoxy)nitrobenzene (6.40 g, 66%) as a white solid.

Workup

  1. washhad been washed
  2. dry with materialdry with methanol
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo (exhaustively at end
  5. customto remove DMF)
  6. customThe residue was chromatographed on silica gel (eluted with 2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bf3fde1f8e8e46eaa6b4afcf8ceb364c
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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