Acetic Anhydride → HCID 86698585, compound

HRID 1054584Notes

Reaction equation

HRID 1054584 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH:8]2[CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH:8]2[CH2:9][N:10]([C:21](=[O:23])[CH3:22])[CH2:11]2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 24902362HCID 24902362, compound

Product 1

HCID 86698585HCID 86698585, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[(4-bromophenoxy)methyl]azetidine (220 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 reaction 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 1 N HCl followed by saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, and concentrated to give 1-{3-[(4-bromophenoxy)methyl]azetidin-1-yl}ethanone (233 mg, 100%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, 2H), 6.78 (d, 2H), 4.28 (m, 1H), 4.24-4.00 (m, 4H), 3.87 (m, 1H), 3.07 (m, 1H), 1.90 (s, 3H)

Workup

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

Sources & evidence

ORD record
ord-dc2a85ef2be24c99a34f7ec5b8e22580
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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