Monobenzone → HCID 2799699, compound

HRID 392393Notes

Reaction equation

HRID 392393 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydride

Product 1

HCID 2799699HCID 2799699, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-benzyloxyphenol (6.01 g, 30 mmol) in anhydrous dimethylformamide (50 ml) under a nitrogen cover was treated with sodium hydride (1.2 g of 60% oil dispersion, 30 mmol) in one portion at room temperature. A moderate gas evolution ensued, and the reaction temperature rose to 41° C. After stirring an additional 35 minutes, 4-Fluoronitrobenzene was added rapidly dropwise, neat via syringe. A mild exotherm brought the reaction temperature to 32° C., after which the reaction was stirred for 18 hours at room temperature. The reaction mixture was poured over ice/water (250 ml), stirred for thirty minutes and the yellow solid collected by suction filtration. Silica gel chromatography (Waters® LC2000; two Pre-Pak® columns, P eluting with 3/1 hexanes/methylene chloride) afforded 4-(4-benzyloxyphenoxy)-1-nitrobenzene (5.9 g, 73%) as a white solid. 1H NMR(400 MHZ): 5.08(2H,s), 6.94-6.99(2H,m), 7.02(4H,s), 7.32-7.47(5H,m), 8.15-8.20(2H,m); MS(ESI)m/z 320.2([M−H]−,100).

Workup

  1. customrose to 41° C
  2. customto 32° C.
  3. stirringafter which the reaction was stirred for 18 hours at room temperature
  4. stirringstirred for thirty minutes
  5. filtrationthe yellow solid collected by suction filtration
  6. washSilica gel chromatography (Waters® LC2000; two Pre-Pak® columns, P eluting with 3/1 hexanes/methylene chloride)

Sources & evidence

ORD record
ord-d9ee581b059c4fe19ce754784b5014c9
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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