Bromine → 5-Bromo-2,3-dihydro-5h-benzo[b]oxepin-4-one

HRID 84614Notes

Reaction equation

HRID 84614 reaction equation
[O:1]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[Br:13]Br>C(OCC)C>[Br:13][CH:4]1[C:5](=[O:8])[CH2:6][CH2:7][O:1][C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]1=2

Participants

4

Reactant 2

HCID 24408BromineHCID 125800312,3,4,5-Tetrahydro-1-benzoxepin-4-one

Product 1

HCID 579004645-Bromo-2,3-dihydro-5h-benzo[b]oxepin-4-oneYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2,3-dihydro-5H-benzo[b]oxepin-4-one (1 eq, 1.6 mmol, 260 mg,), in anhydrous diethyl ether (10 ml), bromine was added dropwise (1.1 eq, 1.76 mmol, 90 ul), and the reaction allowed to stir for an hour. The reaction was absorbed onto silica and purified on the ISCO companion running a gradient from 0% ethyl acetate/petrol to 15% ethyl acetate/petrol, with the product seen at 9% ethyl acetate. This gave 5-bromo-2,3-dihydro-5H-benzo[b]oxepin-4-one as an oil (270 mg, yield 70%).

Workup

  1. customThe reaction was absorbed onto silica
  2. custompurified on the ISCO companion

Sources & evidence

ORD record
ord-9a3e4d26e2b44248b246786f39c21d60
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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