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

HRID 84634Notes

Reaction equation

HRID 84634 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)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. custompurified on silica

Sources & evidence

ORD record
ord-8f6ccecc0c78456c997ba073871a852d
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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