Boron tribromide → ethyl 2-[3-chloro-4-(4,9-dihydroxy-1,3-dioxobenzo[f]isoindol-2-yl)phenyl]acetate

HRID 222427Notes

Reaction equation

HRID 222427 reaction equation
[CH2:1]([O:3][C:4](=[O:44])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:20](=[O:21])[C:19]3[C:18]([O:22]CC4C=CC=CC=4)=[C:17]4[CH:30]=[CH:31][CH:32]=[CH:33][C:16]4=[C:15]([O:34]CC4C=CC=CC=4)[C:14]=3[C:13]2=[O:42])=[C:8]([Cl:43])[CH:7]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:44])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:20](=[O:21])[C:19]3[C:18]([OH:22])=[C:17]4[CH:30]=[CH:31][CH:32]=[CH:33][C:16]4=[C:15]([OH:34])[C:14]=3[C:13]2=[O:42])=[C:8]([Cl:43])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58012507Ethyl (3-chloro-4-{1,3-dioxo-4,9-bis[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

Product 1

HCID 178470686ethyl 2-[3-chloro-4-(4,9-dihydroxy-1,3-dioxobenzo[f]isoindol-2-yl)phenyl]acetateYield 9.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl(3-chloro-4-{1,3-dioxo-4,9-bis[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate (0.505 g, 0.84 mmol) in DCM (30 ml), cooled to −78° C. under an atmosphere of argon, was added boron tribromide (0.24 ml, 2.50 mmol) drop wise. Stirred at −78° C. for 25 minutes. The reaction mixture was quenched with water and warmed to room temperature. This was extracted twice with DCM using a hydrophobic frit. The organic phase was evaporated to an orange solid. Hot trituration in DCM resulted in a yellow solid which was collected by filtration (0.189 g, 0.44 mmol). The filtrate was purified by chromatography on silica gel, eluting with ethyl acetate (0-70%) in hexane to give the title compound as a yellow solid (0.035 g, 0.082 mmol). LC/MS: Rt=3.22, [MH]+ 426.

Workup

  1. customThe reaction mixture was quenched with water
  2. temperaturewarmed to room temperature
  3. extractionThis was extracted twice with DCM using a hydrophobic frit
  4. customThe organic phase was evaporated to an orange solid
  5. customHot trituration in DCM resulted in a yellow solid which
  6. filtrationwas collected by filtration (0.189 g, 0.44 mmol)
  7. customThe filtrate was purified by chromatography on silica gel
  8. washeluting with ethyl acetate (0-70%) in hexane

Sources & evidence

ORD record
ord-450972b8a08b4657a21a6df0f194cfec
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

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