HCID 66700093, compound → HCID 66746269, compound

HRID 1747009Notes

Reaction equation

HRID 1747009 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1>CCOC(C)=O.[Pt]>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 66700093HCID 66700093, compound

Product 1

HCID 66746269HCID 66746269, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,7-dibromodibenzo[b,f]oxepine (10-2) (663 mg, 1.88 mmol) in EtOAc (40 mL) was degassed under N2. Pt/C 10% by wt (200 mg) was added and the reaction was evacuated and placed under H2 gas. After 2 h reaction mixture was degassed and filtered through Celite®545 (eluant EtOAc) and solvent was removed in vacuo to give a yellow oil. The compound was dissolved in petroleum ether and passed through a short pad of SiO2, eluting with isohexanes 400 mL. Solvent was removed in vacuo, to give 2,7-dibromo-10,11-dihydrodibenzo[b,f]oxepine (10-3) (542 mg, 81% yield) as a colorless oil. 1H NMR (CDCl3) δ 7.33-7.32 (1H, m), 7.29-7.24 (2H, m), 7.18-7.14 (1H, m), 7.04-6.96 (2H, m), 3.08 (4H, s) ppm.

Workup

  1. customthe reaction was evacuated
  2. customAfter 2 h reaction mixture
  3. customwas degassed
  4. filtrationfiltered through Celite®545 (eluant EtOAc) and solvent
  5. customwas removed in vacuo
  6. customto give a yellow oil
  7. washeluting with isohexanes 400 mL
  8. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-7e54aed3d56a43d794a7c82615c19df5
Source dataset
uspto-grants-2015_10
Patent number
US09150554B2

Reaction notes

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