Trifluoroacetic acid → Ethyl {4-[4,9-bis(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-2-fluorophenyl}acetate

HRID 889491Notes

Reaction equation

[CH2:1]([O:3][C:4]1[C:12]2[C:11](=O)[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:16]([F:26])[CH:15]=3)[CH:9]([OH:27])[C:8]=2[C:7]([O:28][CH2:29][CH3:30])=[C:6]2[CH:31]=[CH:32][CH:33]=[CH:34][C:5]=12)[CH3:2].C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:16]([F:26])[CH:15]=3)[C:9](=[O:27])[C:8]=2[C:7]([O:28][CH2:29][CH3:30])=[C:6]2[CH:31]=[CH:32][CH:33]=[CH:34][C:5]=12)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl {4-[4,9-bis(ethyloxy)-1-hydroxy-3-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-2-fluorophenyl}acetate (approx. 51.6 mmol) was dissolved in CH2Cl2 (50 ml) and cooled to 0° C. and TFA (50 ml) added. Triethylsilane (12.3 ml, 77 mmol) was added in one portion to give a brown solution. The solution was concentrated in vacuo to give a tan solid. This was recrystallised from hot isopropanol (550 ml), cooled, filtered, washed with isopropanol, and dried in a vacuum oven to give the title compound as off white crystals (20.2 g).

Workup

customto give a brown solution
concentrationThe solution was concentrated in vacuo
customto give a tan solid
customThis was recrystallised from hot isopropanol (550 ml)
temperaturecooled
filtrationfiltered
washwashed with isopropanol
customdried in a vacuum oven

Sources & evidence

ORD record: ord-1ef4c809c89d4f35b8d58ff61bb1a796
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252833B2

Reaction notes

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