[2-Fluoro-3-(1-naphthalenyloxy)-4-nitrophenyl]acetic acid → 1-[(2-Fluoro-3-methyl-6-nitrophenyl)oxy]naphthalene

HRID 1875045Notes

Reaction equation

[F:1][C:2]1[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)=[C:6]([N+:19]([O-:21])=[O:20])[CH:5]=[CH:4][C:3]=1[CH2:22]C(O)=O>C(#N)C.[Cu-]=O>[F:1][C:2]1[C:3]([CH3:22])=[CH:4][CH:5]=[C:6]([N+:19]([O-:21])=[O:20])[C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Copper(I) oxide (1.258 g, 8.79 mmol) was added to a solution of [2-fluoro-3-(1-naphthalenyloxy)-4-nitrophenyl]acetic acid (15.70 g, 46 mmol) in acetonitrile (200 mL). The mixture was heated at 90° C. for 4 hrs. The reaction mixture was concentrated and the residue was purified by flash chromatography (hexane:ethyl acetate) to give the title compound (6.30 g, 36%). ES MS: m/z 298 (M+1), ˜80% pure.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by flash chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record: ord-3c6bddb452bd4450a82cd2a78de30263
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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