Diphenyl Ether → HCID 178526468, compound

HRID 1394118Notes

Reaction equation

HRID 1394118 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1.C(O[C:44](=[O:64])[CH:45]=[C:46]([NH:54][C:55]1[CH:60]=[CH:59][C:58]([N+:61]([O-:63])=[O:62])=[CH:57][CH:56]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([F:53])[CH:48]=1)CCC>>[F:53][C:49]1[CH:48]=[C:47]([C:46]2[CH:45]=[C:44]([OH:64])[C:56]3[C:55](=[CH:60][CH:59]=[C:58]([N+:61]([O-:63])=[O:62])[CH:57]=3)[N:54]=2)[CH:52]=[CH:51][CH:50]=1

Participants

4

Reactant 3

HCID 7583Diphenyl EtherHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 69202260HCID 69202260, compound

Product 1

HCID 178526468HCID 178526468, compoundYield 96%

Conditions

Temperature
250 °C

Procedure

In a 3 L three-neck flask, equipped with mechanical stirrer, Claisen adapter holding a thermocouple probe and reflux condenser with nitrogen inlet was added 0.75 L of Dowtherm A (a eutectic mixture of 26.5% diphenyl and 73.5% diphenyl oxide) The solvent is then preheated to 250° C. To this was cautiously added in small portions 77.0 grams (0.215 moles) of 3-(4-nitro-phenylamino)-3-(3-fluorophenyl)-acrylic acid butyl ester over the course of 0.25 hours. The mixture was maintained at 250° C. for 1.5 hours and then allowed to cool to 90° C. over the course of 2 hours. The mixture was treated with 1.0 L of hexanes, and allowed to cool to room temperature while stirring overnight. The tan solids were collected by suction filtration and washed with three 0.15 L portions of hexanes. The solids were dried under vacuum at 50° C. overnight to yield 58.63 grams (96.0%) of the title compound.

Workup

  1. customIn a 3 L three-neck flask, equipped with mechanical stirrer
  2. temperaturereflux condenser with nitrogen inlet
  3. customis then preheated to 250° C
  4. temperatureto cool to 90° C. over the course of 2 hours
  5. temperatureto cool to room temperature
  6. filtrationThe tan solids were collected by suction filtration
  7. washwashed with three 0.15 L portions of hexanes
  8. customThe solids were dried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-c4f32e0e04694167b509fec87bdc8d6f
Source dataset
uspto-grants-2008_03
Patent number
US07348340B2

Reaction notes

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