Phosphorus oxybromide → HCID 58574545, compound

HRID 1619389Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]=[CH:9][CH:10]2[CH2:14][CH2:13][O:12][C:11]2=O)[CH:3]=1.P(Br)(Br)([Br:18])=O>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:11](=[O:12])[C:10]([CH2:14][CH2:13][Br:18])=[CH:9][N:8]=[C:4]2[CH:3]=1

Participants

Reactant 2

HCID 24613Phosphorus oxybromide

HCID 58574698HCID 58574698, compound

Product 1

HCID 58574545HCID 58574545, compoundYield 86.2%

Procedure

3-((4-bromopyridin-2-ylimino)methyl)dihydrofuran-2(3H)-one (800 mg, 2.97 mmol) and POBr3 (4 g, 13.9 mmol) was stirred at 80° C. for 1.5 hr. After the suspension was poured into ice water, the solution was adjusted to pH 8 and extracted with DCM (3×100 mL). The combined organic layers were washed with brine and concentrated to give 850 mg crude product, which was directly used for the next step without further purification. MS (ESI): 330, 332, 334 (MH+).

Workup

extractionextracted with DCM (3×100 mL)
washThe combined organic layers were washed with brine
concentrationconcentrated

Sources & evidence

ORD record: ord-246285d7027b4611846cf03bdfe194bb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772301B2

Reaction notes

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