Trifluoroacetic acid → 3-bromomethyl-7-nitro-3H-isobenzofuran-1-one

HRID 2251862Notes

Reaction equation

C(O)(C(F)(F)F)=O.C[O:9][C:10](=[O:24])[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:12]=1[C:20](=O)[CH2:21][Br:22].C([SiH](CC)CC)C>C(Cl)Cl>[Br:22][CH2:21][CH:20]1[C:12]2[C:11](=[C:16]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:14][CH:13]=2)[C:10](=[O:9])[O:24]1

Participants

Conditions

Temperature: 70 °C

Procedure

TFA (50 mL) was added to a mixture of 2-(2-bromo-acetyl)-6-nitro-benzoic acid methyl ester (3.47 g, 11.5 mmol, Step D) and 20 mL of triethylsilane in 70 mL of anhydrous CH2Cl2. The mixture was stirred at 70° C. for 48 h, the volatiles were removed under reduced pressure, and hexanes were added to the residue. The titled compound was collected by filtration as an off-white solid.

Workup

customthe volatiles were removed under reduced pressure, and hexanes
additionwere added to the residue
filtrationThe titled compound was collected by filtration as an off-white solid

Sources & evidence

ORD record: ord-ea17061e676a48f681b911c84c13c810
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320992B2

Reaction notes

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