Isopropanol → 4-Fluoro-2-isopropoxy-1-nitrobenzene

HRID 602508Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[C:12]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=CC=C[CH:13]=1.CC(O)C.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH:12]([CH3:17])[CH3:13])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-Fluoro-2-nitrophenol (48 g) was dissolved in dry tetrahydrofuran (THF) (300 mL). Triphenylphosphine (88 g) and 2-propanol (47 mL) were added, and the resulting mixture was cooled to 0° C. Diisopropylazodicarboxylate (66 mL) was added dropwise. The resulting mixture was allowed to warm to room temperature and stirred over night. The solvent was evaporated in vacuo and the resulting mixture was filtered through silica (heptane/ethyl acetate 1:1). The solvent was evaporated in vacuo and the resulting mixture was recrystallised from heptane/ethyl acetate (1:1). The organic phase was separated from the crystalline solid by filtration, the solvent was evaporated in vacuo, and the remaining product was purified by flash chromatography (silica gel, heptane/ethyl acetate 9:1), yielding the title compound as colourless oil (47.2 g, 78%).

Workup

temperatureto warm to room temperature
customThe solvent was evaporated in vacuo
filtrationthe resulting mixture was filtered through silica (heptane/ethyl acetate 1:1)
customThe solvent was evaporated in vacuo
customthe resulting mixture was recrystallised from heptane/ethyl acetate (1:1)
customThe organic phase was separated from the crystalline solid by filtration
customthe solvent was evaporated in vacuo
customthe remaining product was purified by flash chromatography (silica gel, heptane/ethyl acetate 9:1)

Sources & evidence

ORD record: ord-3355035c52ff4b1190983c389afc4ba7
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906537B2

Reaction notes

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