Acetic Anhydride → 1-(2-(4-Bromophenyl)azetidin-1-yl)ethanone

HRID 338333Notes

Reaction equation

HRID 338333 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20].C(OCC)(=O)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:11][CH2:10][N:9]2[C:19](=[O:21])[CH3:20])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 655792352-(4-Bromophenyl)azetidine

Product 1

HCID 866986791-(2-(4-Bromophenyl)azetidin-1-yl)ethanoneYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(4-bromophenyl)azetidine (200 mg, 0.808 mmol) and triethylamine (98 mg, 0.97 mmol) in anhydrous dichloromethane (6 mL) was added acetic anhydride (200 mg, 0.97 mmol). The mixture was stirred at rt for 5 hours. The mixture was poured into ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (100 mg, 49% yield) as a yellow oil that was taken on without further purification.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87ab2b78b06445bba81381c74a19f579
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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