4,6-Dibromoisochroman-1-one → 6-bromo-1H-isochromen-1-one

HRID 1466111Notes

Reaction equation

HRID 1466111 reaction equation
Br[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[C:5](=[O:13])[O:4][CH2:3]1>C(Cl)Cl>[Br:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5](=[O:13])[O:4][CH:3]=[CH:2]2

Participants

3

Reactant 1

HCID 675174614,6-Dibromoisochroman-1-one

Product 1

HCID 212520476-bromo-1H-isochromen-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,6-Dibromo-3,4-dihydro-1H-isochromen-1-one (1.8 g, 5.8 mmol) was dissolved in DCM (15 ml) then added TEA (20 mL, 143 mmol) and stirred at room temperature for 72 hours. The mixture was concentrated then took up the residue with DCM and washed with 1N HCl. Repeated the wash with brine then dried over Na2SO4 and evaporated to dryness. The residue was purified by MPLC with 0-100% EtOAc/hexane to yield 6-Bromo-1H-isochromen-1-one. LC-MS (IE, m/z): 227 [M+2]+.

Workup

  1. concentrationThe mixture was concentrated
  2. washwashed with 1N HCl
  3. washwash with brine
  4. dry with materialthen dried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by MPLC with 0-100% EtOAc/hexane

Sources & evidence

ORD record
ord-0a2346eee1314b6580262ec231704e21
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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