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

HRID 1109677Notes

Reaction equation

HRID 1109677 reaction equation
[N+:1]([C:4]1[CH:45]=[C:44]([F:46])[C:7]([O:8][C:9]2[CH:43]=[CH:42][C:12]([C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([CH3:41])([CH3:40])[C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[C:35]([F:36])=[CH:34][C:33]([N+:37]([O-])=O)=[CH:32][CH:31]=5)=[CH:25][CH:24]=4)[CH:17]=3)([CH3:15])[CH3:14])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)(C)C>[NH2:37][C:33]1[CH:34]=[C:35]([F:36])[C:30]([O:29][C:26]2[CH:27]=[CH:28][C:23]([C:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([C:13]([CH3:15])([CH3:14])[C:12]4[CH:42]=[CH:43][C:9]([O:8][C:7]5[C:44]([F:46])=[CH:45][C:4]([NH2:1])=[CH:5][CH:6]=5)=[CH:10][CH:11]=4)[CH:17]=3)([CH3:40])[CH3:41])=[CH:24][CH:25]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 867479171,3-Bis[4-(4-nitro-6-fluorophenoxy)-alpha, alpha-dimethylbenzyl]benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 225986341,3-Bis[4-(4-amino-6-fluorophenoxy)-alpha, alpha-dimethylbenzyl]benzeneYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

Successively, to a reduction vessel equipped with a thermometer, reflux condenser and stirrer, 115 g (0.184 mol) of 1,3-bis[4-(4-nitro-6-fluorophenoxy)-α, α-dimethylbenzyl]benzene, 250 g of isopropyl alcohol and 4.8 g of 5%-Pd/c having a moisture content of 50% were charged and reacted at 70°~80° C. for 4 hours in a hydrogen atmosphere. After finishing the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure to obtain 84.2 g (81% yield) of 1,3-bis[4-(4-amino-6-fluorophenoxy)-α, α-dimethylbenzyl]benzene as a light yellow crystal having a melting point of 130.4~132.9.

Workup

  1. customSuccessively, to a reduction vessel equipped with a thermometer
  2. temperaturereflux condenser and stirrer
  3. additionwere charged
  4. customthe reaction
  5. filtrationthe catalyst was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-23daf556b28d401ab1dae3c4c46bba2c
Source dataset
uspto-grants-1994_06
Patent number
US05321096

Reaction notes

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