3,4-Dichlorophenol → 3-(3,4-Dichlorophenoxy)-1-(diphenylmethyl)azetidine

HRID 1182089Notes

Reaction equation

HRID 1182089 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[CH:12]([N:25]1[CH2:28][CH:27](OS(C)(=O)=O)[CH2:26]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH:12]([N:25]1[CH2:28][CH:27]([O:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:26]1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 24758Sodium hydrideHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 150422273-(3,4-Dichlorophenoxy)-1-(diphenylmethyl)azetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3,4 dichlorophenol (4.12 g, 25.3 mmol) in DMF (150 ml) under argon is treated with a 60% dispersion of sodium hydride in mineral oil (40.4 mmol) and the reaction mixture stirred for 10 minutes. A solution of Methanesulfonic acid 1-benzhydryl-azetidin-3-yl ester (7.27 g, 22.96 mmol) in DMF (50 ml) is added and the reaction mixture left to stir at 60° C. for 20 hours. The reaction mixture is partitioned between ethylacetate and water. The organic phase is washed with water (×2), dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (elution with 1:4 ethylacetate/isohexane) to afford 1-Benzhydryl-3-(3,4-dichloro-phenoxy)-azetidine. [M+H] 383.8

Workup

  1. waitthe reaction mixture left
  2. stirringto stir at 60° C. for 20 hours
  3. customThe reaction mixture is partitioned between ethylacetate and water
  4. washThe organic phase is washed with water (×2)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe crude product is purified by flash silica chromatography (elution with 1:4 ethylacetate/isohexane)

Sources & evidence

ORD record
ord-12e935f634964ef09e49b5b1d91fb516
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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