Boron tribromide → Ethyl {3-chloro-4-[4-(ethyloxy)-9-hydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetate

HRID 222433Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:39])[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][CH2:23][C:24]4C=CC=CC=4)=[C:17]4[CH:30]=[CH:31][CH:32]=[CH:33][C:16]4=[C:15]([O:34]CC)[C:14]=3[C:13]2=[O:37])=[C:8]([Cl:38])[CH:7]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[Cl:38][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:39])[CH:11]=[CH:10][C:9]=1[N:12]1[C:13](=[O:37])[C:14]2[C:15]([OH:34])=[C:16]3[CH:33]=[CH:32][CH:31]=[CH:30][C:17]3=[C:18]([O:22][CH2:23][CH3:24])[C:19]=2[C:20]1=[O:21]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of ethyl(3-chloro-4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate (1.75 g, 3.22 mmol) in DCM (40 ml), cooled to −78° C. under an atmosphere of argon, was added boron tribromide (0.31 ml, 3.22 mmol) drop wise. Stirred at −78° C. for 12 minutes. A further addition of boron tribromide (0.31 ml, 3.22 mmol) was made drop wise. 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 yellow solid. This was purified by chromatography on silica gel, eluting with ethyl acetate (0-60%) in hexane to give the title compound as a orange oily solid (0.920 g, 2.03 mmol). LC/MS: Rt=3.65, [MH]+ 454.

Workup

customThe reaction mixture was quenched with water
temperaturewarmed to room temperature
extractionThis was extracted twice with DCM using a hydrophobic frit
customThe organic phase was evaporated to an yellow solid
customThis was purified by chromatography on silica gel
washeluting with ethyl acetate (0-60%) in hexane

Sources & evidence

ORD record: ord-42925e32dd504d1dbfb7dd5eab39b232
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207213B2

Reaction notes

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