Sodium hydride → 4-[3-(2-Nitro-4-trifluoromethanesulfonyl-phenoxy)-phenoxy]-benzoic acid

HRID 1358748Notes

Reaction equation

HRID 1358748 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1.[H-].[Na+].[N+:20]([C:23]1[CH:28]=[C:27]([S:29]([C:32]([F:35])([F:34])[F:33])(=[O:31])=[O:30])[CH:26]=[CH:25][C:24]=1Cl)([O-:22])=[O:21]>>[N+:20]([C:23]1[CH:28]=[C:27]([S:29]([C:32]([F:35])([F:33])[F:34])(=[O:30])=[O:31])[CH:26]=[CH:25][C:24]=1[O:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)([O-:22])=[O:21]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 6153894-(3-Hydroxyphenoxy)benzoic acidHCID 15479561-chloro-2-nitro-4-[(trifluoromethyl)sulfonyl]benzene

Product 1

HCID 99349834-[3-(2-Nitro-4-trifluoromethanesulfonyl-phenoxy)-phenoxy]-benzoic acid

Procedure

Using procedure as in example 10, a reaction of 4-(3-hydroxyphenoxy)benzoic acid (100 mg, 0.4334 mmol), NaH (38 mg, 2.2 equiv.) and 2-nitro-4-(trifluoromethylsulfonyl)chlorobenzene (126 mg, 1 equiv.) afforded 4-[3-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-phenoxy]-benzoic acid. 1HNMR (360 MHz, DMSO-d6) δ 12.8 (br s, 1H, COOH), 8.75 (d, J=2.7 Hz, 1H), 8.30 (dd, J=2.7 & 9.0 Hz, 1H), 7.95 (m, 2H), 7.6 (m, 1H), 7.37 (d, J=9.0 Hz, 1H), 7.17-7.21 (m, 2H), 7.12 (m, 3H). MS-EI m/z 483 [M+].

Sources & evidence

ORD record
ord-eb24a9088b3a41f287c11cc93107b919
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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