Acetic Anhydride → 1-(3-(4-Bromophenoxy)azetidin-1-yl)ethanone

HRID 338237Notes

Reaction equation

HRID 338237 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH:7]2[CH2:10][NH:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH:7]2[CH2:8][N:9]([C:20](=[O:22])[CH3:21])[CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 249023583-(4-Bromophenoxy)azetidine

Product 1

HCID 866985821-(3-(4-Bromophenoxy)azetidin-1-yl)ethanoneYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-bromophenoxy)azetidine (207 mg, 0.91 mmol) in CH2Cl2 (10 mL) was added triethylamine (276 mg, 2.73 mmol) and acetic anhydride (186 mg, 1.82 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to give a yellow oil. The crude product was diluted with ethyl acetate (20 mL), washed with 1N HCl and saturated NaHCO3, dried over sodium sulfate, and concentrated in vacuo to give 1-[3-(4-bromophenoxy)azetidin-1-yl]ethanone (245 mg, 100%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.40 (d, 2H), 6.61 (d, 2H), 4.89 (m, 1H), 4.49 (m, 1H), 4.37 (m, 1H), 4.17 (m, 1H), 4.03 (m, 1H), 1.90 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a yellow oil
  3. washwashed with 1N HCl and saturated NaHCO3
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fccc59a3df954415be06fc4bd4e20550
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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