Sodium hydride → 7-Bromo-3,4-dihydro-1-benzoxepin-5(2H)-one

HRID 1629079Notes

Reaction equation

HRID 1629079 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][CH2:15]Br)=[C:8]([C:10](=[O:12])[CH3:11])[CH:9]=1>C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[O:13][CH2:14][CH2:15][CH2:11][C:10](=[O:12])[C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 582041051-[5-Bromo-2-(2-bromoethoxy)phenyl]ethanone

Product 1

HCID 106815487-Bromo-3,4-dihydro-1-benzoxepin-5(2H)-oneYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of NaH (60% dispersion in mineral oil) (1.48 g, 37.1 mmol) in THF (50 mL) at room temperature was added [5-bromo-2-(2-bromo-ethoxy)-phenyl]-ethanone (8.07 g, 25.1 mmol). The reaction mixture was slowly heated to reflux and allowed to stir for 20 h. The solvent was removed in vacuo and the residue subjected to flash chromatography (SiO2, 4:1 ethyl acetate/petroleum ether) to give 7-Bromo-3,4-dihydro-2H-benzo[b]oxepin-5-one as a yellow oil (4.22 g, 70%). 1H NMR (CDCl3) δ 2.15-2.29 (2H, m), 2.89 (2H, t, J=7.0 Hz), 4.24 (2H, t, J=6.6 Hz), 6.97 (1H, d, J=8.8 Hz), 7.50 (1H, dd, J=2.6, 8.1 Hz), 7.87 (1H, d, J=2.6 Hz).

Workup

  1. temperatureThe reaction mixture was slowly heated
  2. temperatureto reflux
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7a93af84a894409e9dd78b816591b209
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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