Potassium Carbonate → Ethyl 2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate

HRID 365115Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([F:16])[CH:15]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Cl[CH2:18][CH2:19][NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([F:16])[CH:15]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:18][CH2:19][NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(3,5-difluorophenoxy)phenol (0.50 g), ethyl N-2-chloroethylcarbamate (0.375 g), potassium carbonate (0.621 g) and anhydrous dimethylformamide (10 ml) was stirred at 100° C. for 3 hours, followed by cooling to room temperature. Ice-water (50 ml) was poured to the resultant mixture, which was extracted with toluene (50 ml). The toluene extract was washed with water and dried over anhydrous sodium sulfate. The toluene extract was concentrated under reduced pressure to give an oily residue. The residue was purified by silica gel column chromatography to give 0.605 g of ethyl N-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate as a colorless liquid. nD25.5 1.5305.

Workup

temperatureby cooling to room temperature
extractionwas extracted with toluene (50 ml)
extractionThe toluene extract
washwas washed with water
dry with materialdried over anhydrous sodium sulfate
extractionThe toluene extract
concentrationwas concentrated under reduced pressure
customto give an oily residue
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a0b78a5315134ffab3d780be27e84638
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04608389

Reaction notes

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