Water → 4-[2-(2-Fluoro-4-nitrophenoxy)ethyl]morpholine

HRID 56260Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 1,2-difluoro-4-nitrobenzene (1.0 g, 6.29 mmol), 2-morpholinoethanol (1.0 g, 7.62 mmol) and Cs2CO3 in DMF (10 mL) was stirred at 75° C. for 12 h. 30 mL of water was then added and the resulting mixture was extracted with DCM (30 mL×2). The combined organic phases were washed with brine (30 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as yellow oil (1.30 g, 76%).

Workup

extractionthe resulting mixture was extracted with DCM (30 mL×2)
washThe combined organic phases were washed with brine (30 mL×3)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

Sources & evidence

ORD record: ord-8556e0a10d2245e59d74de65968a0b5e
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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