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

HRID 913166Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18]CC3C=CC=CC=3)=[C:13]3[CH:26]=[CH:27][CH:28]=[CH:29][C:12]3=[C:11]([O:30]CC3C=CC=CC=3)[C:10]=2[C:9]1=[O:38].B(Br)(Br)Br>C(Cl)Cl>[CH2:43]([O:42][C:40](=[O:41])[CH2:39][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[C:16](=[O:17])[C:15]3[C:14]([OH:18])=[C:13]4[CH:26]=[CH:27][CH:28]=[CH:29][C:12]4=[C:11]([OH:30])[C:10]=3[C:9]2=[O:38])=[C:2]([Cl:1])[CH:3]=1)[CH3:44]

Participants

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 X2 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, 53%). 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

customThe reaction mixture was quenched with water
temperaturewarmed to room temperature
extractionThis was extracted X2 with DCM using a hydrophobic frit
customThe organic phase was evaporated to an orange solid
customHot trituration in DCM resulted in a yellow solid which
filtrationwas collected by filtration (0.189 g, 0.44 mmol, 53%)
customThe filtrate was purified by chromatography on silica gel
washeluting with ethyl acetate (0-70%) in hexane

Sources & evidence

ORD record: ord-fbcc84b12f934c208fa972109393d7dc
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026270B2

Reaction notes

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