Hydrogen Bromide → HCID 53639162, compound

HRID 485405Notes

Reaction equation

HRID 485405 reaction equation
C(OC([C:6](=[C:11]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:7][C:8]([OH:10])=[O:9])=O)C.Br>C(O)(=O)C>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 544389311-Ethyl 2-[(4-fluorophenyl)phenylmethylene]butanedioate

Product 1

HCID 53639162HCID 53639162, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Ethoxycarbonyl-4-(4-fluorophenyl)-4-phenylbut-3-enoic acid (47 g., 0.143 mole) was added to a mixture of glacial acetic acid (1000 ml.) and 48% aqueous hydrobromic acid (500 ml.), and the resulting mixture stirred at reflux for 16 hours. The reaction mixture was then concentrated under vacuum and the concentrate extracted with ether (3×500 ml.). The combined ether extract was extracted with 4% aqueous ammonium hydroxide (5×200 ml.). The combined aqueous extract was acidified with 6N hydrochloric acid to a pH of 6.5 and extracted again with ether (3×250 ml.). The combined ether extract was dried (MgSO4), filtered and evaporated under vacuum to an oil, which solidified on standing. Trituration with hexane gave 15 g. of the named product (47% yield, m.p. 98°-100° C., elemental analysis calculated: 74.99% C.; 5.11% H; 7.41% F; found: 74.69% C; 5.40% H; 7.17% F).

Workup

  1. temperatureat reflux for 16 hours
  2. concentrationThe reaction mixture was then concentrated under vacuum
  3. extractionthe concentrate extracted with ether (3×500 ml.)
  4. extractionThe combined ether extract
  5. extractionwas extracted with 4% aqueous ammonium hydroxide (5×200 ml.)
  6. extractionThe combined aqueous extract
  7. extractionextracted again with ether (3×250 ml.)
  8. extractionThe combined ether extract
  9. dry with materialwas dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated under vacuum to an oil, which
  12. customTrituration with hexane gave 15 g

Sources & evidence

ORD record
ord-1329855ecefa489d8933f7d0e487e127
Source dataset
uspto-grants-1985_08
Patent number
US04536518

Reaction notes

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