Potassium Carbonate → 1,3-Bis[4-(4-nitro-6-fluorophenoxy)-alpha, alpha-dimethylbenzyl]benzene

HRID 1109676

Reaction equation

HRID 1109676 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[OH:12][C:13]1[CH:37]=[CH:36][C:16]([C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)([CH3:28])[CH3:27])[CH:21]=2)([CH3:19])[CH3:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:9]([C:4]1[CH:3]=[C:2]([F:1])[C:7]([O:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([CH3:27])([CH3:28])[C:29]4[CH:30]=[CH:31][C:32]([O:35][C:7]5[C:2]([F:1])=[CH:3][C:4]([N+:9]([O-:11])=[O:10])=[CH:5][CH:6]=5)=[CH:33][CH:34]=4)[CH:21]=3)([CH3:19])[CH3:18])=[CH:36][CH:37]=2)=[CH:6][CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 3292100Phenol, 4,4'-[1,3-phenylenebis(1-methylethylidene)]bis-

Product 1

HCID 867479171,3-Bis[4-(4-nitro-6-fluorophenoxy)-alpha, alpha-dimethylbenzyl]benzeneYield 104.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a reaction vessel equipped with a thermometer, reflux condenser and a stirrer, 200 g of N,N-dimethylformamide (DMF), 65 g (0.409 mol) of 3,4-difluoronitrobenzene, 69.1 g (0.199 mol) of 1,3-bis(4-hydroxycumyl) benzene and 33.1 g (0.239 mol) of potassium carbonate were charged and warmed to 80° C. with stirring. After aging the mixture at 80° C. for 6 hours, inorganic salts was removed by filtration. The filtrate was mixed with 50 ml of water and cooled to the room temperature. The precipitated crystal was filtered and slugged with isopropyl alcohol to obtain 129.4 g (97% yield) of 1,3-bis[4-(4-nitro-6-fluorophenoxy)-α, α-dimethylbenzyl]benzene having a melting point of 150.7°~151.8° C.

Workup

  1. customTo a reaction vessel equipped with a thermometer
  2. temperaturereflux condenser and a stirrer
  3. customat 80° C.
  4. customfor 6 hours
  5. custominorganic salts was removed by filtration
  6. additionThe filtrate was mixed with 50 ml of water
  7. temperaturecooled to the room temperature
  8. filtrationThe precipitated crystal was filtered

Sources & evidence

ORD record
ord-7dd67369127c40c986d251e420e58aa8
Source dataset
uspto-grants-1994_06
Patent number
US05321096

Linked notes

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