Trifluoroacetic acid → 3-(2,4-Dichlorophenoxy)azetidine

HRID 522905Notes

Reaction equation

HRID 522905 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[O:4][CH:5]1[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[O:4][CH:5]1[CH2:8][NH:7][CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67354747Tert-butyl 3-(2,4-dichlorophenoxy)azetidine-1-carboxylate

Product 1

HCID 534091833-(2,4-Dichlorophenoxy)azetidineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(2,4-dichlorophenoxy)azetidine-1-carboxylate (1.2 g, 3.78 mmol) in CH2Cl2 (10 mL) was added trifluoroacetic acid (TFA) (7 mL) and the reaction mixture was stirred at RT for 2 h. The mixture was concentrated under reduced pressure and filtered, washing with chloroform followed by diethyl ether to obtain 3-(2,4-dichlorophenoxy) azetidine (0.800 g, 100%) as a TFA salt.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. filtrationfiltered
  3. washwashing with chloroform

Sources & evidence

ORD record
ord-2792ccd22e434f51b05e19f96909c590
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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