Diphenyl Ether → HCID 178515591, compound

HRID 1071840Notes

Reaction equation

HRID 1071840 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:62])[CH:45]=[C:46]([NH:54][C:55]1[CH:60]=[CH:59][C:58]([Br:61])=[CH:57][CH:56]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([F:53])[CH:48]=1)CCC>CCCCCC>[Br:61][C:58]1[CH:59]=[C:60]2[C:55](=[CH:56][CH:57]=1)[N:54]=[C:46]([C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([F:53])[CH:48]=1)[CH:45]=[C:44]2[OH:62]

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 68882197HCID 68882197, compound

Product 1

HCID 178515591HCID 178515591, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
250 °C

Procedure

Dowtherm A (a eutectic mixture of 26.5% diphenyl and 73.5% diphenyl oxide) (1.2 L) was charged into a round-bottom flask equipped with a condenser, magnetic stirrer, thermocouple, heating mantle with a variable voltage controller, and a nitrogen inlet, and heated to 250° C. To this was cautiously added in small portions 48 g (0.11 moles) of 3-(4-bromophenylamino)-3-(3-fluorophenyl)-acrylic acid butyl ester. As portions were added gas was evolved and foaming occurred. Crystals of product began to form and adhere to the sides. After all the material had been added the heating of the reaction was continued for 1 hour. The mixture was then cooled to room temperature and hexane was added. A solid product was collected by vacuum filtration and washed with hexane. After drying in a vacuum oven, 35.7 g (90%) of product was recovered.

Workup

  1. additionwas charged into a round-bottom flask
  2. customequipped with a condenser, magnetic stirrer
  3. temperaturethermocouple, heating mantle with a variable voltage controller, and a nitrogen inlet
  4. additionAs portions were added gas
  5. customto form
  6. additionAfter all the material had been added the
  7. temperatureheating of the reaction
  8. temperatureThe mixture was then cooled to room temperature
  9. filtrationA solid product was collected by vacuum filtration
  10. washwashed with hexane
  11. dry with materialAfter drying in a vacuum oven, 35.7 g (90%) of product
  12. customwas recovered

Sources & evidence

ORD record
ord-b49b84f9f6bd462892ec6b21b4575ea8
Source dataset
uspto-grants-2005_06
Patent number
US06906193B2

Reaction notes

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