2,4-Dichlorophenol → Tert-butyl 3-(2,4-dichlorophenoxy)azetidine-1-carboxylate

HRID 522904Notes

Reaction equation

HRID 522904 reaction equation
S([O:11][CH:12]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1)(C1C=CC(C)=CC=1)(=O)=O.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[O:11][CH:12]1[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:15]1

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 57351432tert-Butyl 3-(tosyloxy)azetidine-1-carboxylate

Product 1

HCID 67354747Tert-butyl 3-(2,4-dichlorophenoxy)azetidine-1-carboxylateYield 123.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of tert-butyl 3-(tosyloxy)azetidine-1-carboxylate (1.0 g, 3.05 mmol) and 2,4-dichlorophenol (0.490 g, 3.05 mmol) in DMF (10 mL) was added potassium carbonate (0.630 g, 4.67 mmol) and the reaction mixture was heated to 120° C. for 2 h. Then reaction was quenched with water and extracted with EtOAc (2×25 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided tert-butyl 3-(2,4-dichlorophenoxy)azetidine-1-carboxylate (1.2 g, 63%) as a solid.

Workup

  1. customThen reaction
  2. customwas quenched with water
  3. extractionextracted with EtOAc (2×25 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-60f6d704208c442980d3c97cfe394678
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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