Hydrogen Bromide → HCID 19983091, compound

HRID 1460233Notes

Reaction equation

HRID 1460233 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)([CH:11]2[CH2:15][CH2:14][N:13](S(C3C=CC(C)=CC=3)(=O)=[O:17])[CH2:12]2)[C:9]#[N:10])=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.Br.[C:41]([O-:46])(=[O:45])[C:42]([O-:44])=[O:43]>C(Cl)(Cl)Cl>[OH2:17].[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)([CH:11]2[CH2:15][CH2:14][NH:13][CH2:12]2)[C:9]#[N:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 996PhenolHCID 71081OxalateHCID 15020356HCID 15020356, compound

Product 1

HCID 19983091HCID 19983091, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of α,α-bis(4-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-3-pyrrolidineacetonitrile (16.6 g, 0.0367 mole), phenol (50 g, 0.53 mole) and 300 ml of 48% hydrobromic acid was heated at reflux for two hours. The reaction mixture was cooled to room temperature and made alkaline with ice/50% sodium hydroxide. The aqueous layer was extracted with chloroform. The chloroform layer was back extracted with 5% sodium hydroxide, dried over sodium sulfate and filtered, and solvent was removed to produce a dark brown oil. The dark-brown oil was dissolved in chloroform and extracted with 1N sulfuric acid. This acidic layer was discarded. The chloroform layer was extracted with base, and the solvent was removed to give a dark brown oil. This oil was converted to the oxalate, and the salt was recrystallized from methanol-diethyl ether. A white solid was isolated and dried in vacuo overnight at 80° C. This produced 7.17 g (49%) of off-white solid, mp 88.5°-90° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two hours
  3. extractionThe aqueous layer was extracted with chloroform
  4. extractionThe chloroform layer was back extracted with 5% sodium hydroxide
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customsolvent was removed
  8. customto produce a dark brown oil
  9. extractionextracted with 1N sulfuric acid
  10. extractionThe chloroform layer was extracted with base
  11. customthe solvent was removed
  12. customto give a dark brown oil
  13. customthe salt was recrystallized from methanol-diethyl ether
  14. customA white solid was isolated
  15. customdried in vacuo overnight at 80° C

Sources & evidence

ORD record
ord-40c567f8e19f42189965cb806d527003
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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