Phenyl chloroformate → 1-Phenoxycarbonyl-3-(p-fluorophenoxy)azetidine

HRID 437577

Reaction equation

HRID 437577 reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:26]1([O:32][C:33](Cl)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[O:32]([C:33]([N:14]1[CH2:17][CH:16]([O:18][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH2:15]1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 150533691-Benzhydryl-3-(4-fluorophenoxy)azetidine

Product 1

HCID 214287381-Phenoxycarbonyl-3-(p-fluorophenoxy)azetidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 20.0 g of 1-benzhydryl-3-(4-fluorophenoxy)azetidine and 10.3 g of phenylchloroformate in 200 ml. of toluene is refluxed for 16 hours. The reaction mixture is cooled, and the toluene is removed under reduced pressure to give a yellow oil. The oil is triturated with hexane to give a white solid of 1-phenoxycarbonyl-3-(p-fluorophenoxy)azetidine.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe toluene is removed under reduced pressure
  3. customto give a yellow oil
  4. customThe oil is triturated with hexane

Sources & evidence

ORD record
ord-f1f12d4a48a34596b18ae613aeac5c68
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Linked notes

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