Bromine → 4-Bromo-3,4-dihydro-1-benzoxepin-5(2H)-one

HRID 84525

Reaction equation

HRID 84525 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[Br:13]Br>C(OCC)C>[Br:13][CH:5]1[CH2:6][CH2:7][O:1][C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]1=[O:8]

Participants

4

Reactant 2

HCID 24408BromineHCID 3155752,3,4,5-Tetrahydro-1-benzoxepin-5-one

Product 1

HCID 138632344-Bromo-3,4-dihydro-1-benzoxepin-5(2H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3,4-dihydro-2H-benzo[b]oxepin-5-one (3.10 g, 12.8 mmol) in diethyl ether at 0° C., bromine (625 μl, 12.2 mmol) was added and stirred for 2.5 hours, gradually raising the temperature to room temperature. Purification on silica and triturating using diethyl ether and hexanes gave 4-bromo-3,4-dihydro-2H-benzo[b]oxepin-5-one.

Workup

  1. customPurification on silica
  2. customtriturating

Sources & evidence

ORD record
ord-2c48424fc66e4bfbbf7a255b7d0ce46f
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Linked notes

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