5-Fluoro-2-nitrophenol → 4-(2-(5-Fluoro-2-nitrophenoxy)ethyl)morpholine

HRID 415084Notes

Reaction equation

CS([O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)(=O)=O.[F:14][C:15]1[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19](O)[CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(N(C)C)=O>C(OCC)(=O)C>[F:14][C:15]1[CH:20]=[CH:19][C:18]([N+:22]([O-:24])=[O:23])=[C:17]([CH:16]=1)[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 90 °C

Procedure

A flask was charged with 2-morpholinoethyl methanesulfonate (1.5 g, 6.9 mmol), 5-fluoro-2-nitrophenol (0.99 g, 6.3 mmol), cesium carbonate (4.0 g, 12 mmol) and DMA (100 mL), and the reaction mixture was heated to 90° C. for 15 hours. Ethyl acetate (200 ml) was added to the cooled reaction mixture and the mixture was extracted with water (2×100 ml), 1N sodium hydroxide (2×50 ml) and aqueous 5% lithium chloride (2×50 ml). The organic solvent was removed on a rotary evaporator under reduced pressure. Purified of the crude product by silica column chromatography using 50:50 ethyl acetate:hexanes as eluant gave 0.71 g of 4-(2-(5-fluoro-2-nitrophenoxy)ethyl)morpholine (39% yield). EI (MS): 271 (MH+).

Workup

extractionthe mixture was extracted with water (2×100 ml), 1N sodium hydroxide (2×50 ml) and aqueous 5% lithium chloride (2×50 ml)
customThe organic solvent was removed on a rotary evaporator under reduced pressure
customPurified of the crude product by silica column chromatography

Sources & evidence

ORD record: ord-72cd71e5c5fa4c2c872431d6d08469fb
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088767B2

Reaction notes

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