Sodium hydride → {4-[4-(2-Nitro-4-trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy}-acetic acid ethyl ester

HRID 1358750Notes

Reaction equation

HRID 1358750 reaction equation
[OH:1][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.[H-].[Na+].[N+:26]([C:29]1[CH:34]=[C:33]([S:35]([C:38]([F:41])([F:40])[F:39])(=[O:37])=[O:36])[CH:32]=[CH:31][C:30]=1Cl)([O-:28])=[O:27]>>[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:4]=[CH:3][C:2]([O:1][C:30]3[CH:31]=[CH:32][C:33]([S:35]([C:38]([F:40])([F:41])[F:39])(=[O:37])=[O:36])=[CH:34][C:29]=3[N+:26]([O-:28])=[O:27])=[CH:7][CH:6]=2)(=[O:9])=[O:10])=[CH:12][CH:13]=1)[CH3:21]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzeneHCID 3614055Ethyl [4-(4-hydroxyphenylsulfonyl)phenoxy)acetate

Product 1

HCID 9873218{4-[4-(2-Nitro-4-trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy}-acetic acid ethyl ester

Procedure

Using procedure as in example 10, a reaction of ethyl [4-(4-hydroxyphenylsulfonyl)phenoxy]acetate (100 mg, 0.297 mmol), NaH (13 mg, 1.1 equiv.) and 2-nitro-4-(trifluoromethylsulfonyl)chlorobenzene (86 mg, 1 equiv.) afforded{4-[4-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy}-acetic acid ethyl ester. 1HNMR (300 MHz, DMSO-d6) δ 8.79 (d, J=2.3 Hz, 1H), 8.29 (dd, J=2.3 & 9.0 Hz, 1H), 8.07 (d, J=8.9 Hz, 2H), 7.92 (d, J=8.9 Hz, 2H), 7.52 (d, J=8.9 Hz, 2H), 7.47 (d, J=9.0 Hz, 1H), 7.14 (d, J=8.9 Hz, 2H), 4.91 (s, 2H, CH2), 4.15 (q, J=7.2 Hz, 2H, OCH2CH3), 1.19 (t, J=7.2 Hz, 3H, OCH2CH3). MS-EI m/z 589 [M+].

Sources & evidence

ORD record
ord-6a367ce40e06449cbb8c8d7e76ca7d53
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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