Water → {4-[(4-Trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy)-acetic acid ethyl ester

HRID 1358752Notes

Reaction equation

O[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:23]=[CH:22][C:14]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:24][C:25]([F:37])([F:36])[S:26]([C:29]1[CH:34]=[CH:33][C:32](Cl)=[CH:31][CH:30]=1)(=[O:28])=[O:27].C(=O)([O-])[O-:39].[K+].[K+].O>CN(C=O)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:15][C:14]1[CH:22]=[CH:23][C:11]([S:8]([C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=2[O:39][C:32]2[CH:33]=[CH:34][C:29]([S:26]([C:25]([F:37])([F:36])[F:24])(=[O:28])=[O:27])=[CH:30][CH:31]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1)[CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl [4-(4-hydroxyphenylsulfonyl)phenoxy]acetate (100 mg, 0.3 mmol), 4-(trifluoromethylsulfonyl)chlorobenzene (73 mg, 1 equiv.) and potassium carbonate (164 mg, 4 equiv.) in DMF was heated to 100° C. overnight. The reaction was poured into water, extracted with EtOAc, washed with organic layer with water, brine, dried and concentrated. The residue was column chromatographed to give{4-[4-(4-trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy}-acetic acid ethyl ester. 1HNMR (300 MHz, DMSO-d6) δ 8.11 (d, J=8.92 Hz, 2H), 8.03 (d, J=8.77 Hz, 2H), 7.90 (d, J=8.98 Hz, 2H), 7.39-7.43 (m, 4H), 7.14 (d, J=8.77 Hz, 2H), 4.90 (s, 2H, CH2), 4.15 (q, J=7.02 Hz, 2H, OCH2CH3), 1.19 (t, J=7.02 Hz, 3H, OCH2CH3). MS-EI m/z 544 [M+].

Workup

extractionextracted with EtOAc
washwashed with organic layer with water, brine
customdried
concentrationconcentrated
customchromatographed to give{4-[4-(4-trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy}-acetic acid ethyl ester

Sources & evidence

ORD record: ord-54fd802a6d85496e8c30140bcbd70b79
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06596772B1

Reaction notes

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