Bromine → 4,7-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

HRID 628046Notes

Reaction equation

HRID 628046 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[Br:14]Br>C(OCC)C>[Br:14][CH:9]1[CH2:8][CH2:7][O:6][C:5]2[CH:12]=[CH:13][C:2]([Br:1])=[CH:3][C:4]=2[C:10]1=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 106815487-Bromo-3,4-dihydro-1-benzoxepin-5(2H)-one

Product 1

HCID 579004584,7-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 7-bromo-3,4-dihydro-2H-benzo[b]oxepin-5-one (700 mg) in diethyl ether (20 mL) at 0° C. was added bromine (0.14 mL) dropwise and the reaction was stirred at room temperature for 16 h. The reaction was then quenched with aqueous sodium thiosulfate solution (30 mL) and the product extracted into diethyl ether (2×30 mL) The combined organics were dried (MgSO4), reduced in vacuo and purified on silica to give 4,7-dibromo-3,4-dihydro-2H-benzo[b]oxepin-5-one.

Workup

  1. customThe reaction was then quenched with aqueous sodium thiosulfate solution (30 mL)
  2. extractionthe product extracted into diethyl ether (2×30 mL) The combined
  3. dry with materialorganics were dried (MgSO4)
  4. custompurified on silica

Sources & evidence

ORD record
ord-5e5d1d58b2854329bfb1249dc3093497
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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