N-bromobutanimide → HCID 13187506, compound

HRID 705430Notes

Reaction equation

HRID 705430 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH3:9].C1C(=O)N([Br:21])C(=O)C1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH2:9][Br:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 3143021-(2-chloro-4-nitrophenyl)ethanone

Product 1

HCID 13187506HCID 13187506, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A stirring solution of 3-chloro-4-acetyl-nitrobenzene (1.685 g, 8.44 mmol) (prepared as described in J. Med. Chem. 2005, 48, 6066) and paratoluenesulfonic acid (2.41 g, 12.66 mmol) in acetonitrile (100 mL) was treated with NBS (1.503 g, 8.44 mmol) and heated to 80° C. for 23 h. Another gram of NBS was added after 21 h. The reaction was cooled to room temperature and concentrated in vacuo. The residue was taken up in EtOAc and the organic layer was washed with water (2×), brine, and dried over MgSO4, filtered, and adsorbed on silica. Purification on silica by flash chromatography using a gradient of 0-40% EtOAc/hexane yielded 554 mg of the titled compound as a waxy solid (23% yield): 1H NMR (400 MHz, DMSO-d6) δ 4.95 (s, 2H), 8.09 (d, 1H), 8.35 (dd, 1H), 8.44 (d, 1H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. washthe organic layer was washed with water (2×), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customPurification on silica by flash chromatography

Sources & evidence

ORD record
ord-e3f420663f7f432ca34e989d64ebe964
Source dataset
uspto-grants-2015_11
Patent number
US09174949B2

Reaction notes

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