Sodium hydride → HCID 9868320, compound

HRID 1358747Notes

Reaction equation

HRID 1358747 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][OH:13])=[CH:6][C:5]=1C.[H-].[Na+].[N+:18]([C:21]1[CH:26]=[C:25]([S:27]([C:30]([F:33])([F:32])[F:31])(=[O:29])=[O:28])[CH:24]=[CH:23][C:22]=1Cl)([O-:20])=[O:19]>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][O:13][C:22]2[CH:23]=[CH:24][C:25]([S:27]([C:30]([F:32])([F:33])[F:31])(=[O:29])=[O:28])=[CH:26][C:21]=2[N+:18]([O-:20])=[O:19])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzeneHCID 69632005HCID 69632005, compound

Product 1

HCID 9868320HCID 9868320, compound

Procedure

Using procedure as in Example 10, a reaction of methyl 4-(2-hydroxyethoxy)benzoic acid methyl ester (100 mg, 0.51 mmol), NaH (22 mg, 1.1 equiv.) and 2-nitro-4-(trifluoromethylsulfonyl)chlorobenzene (148 mg, 1 equiv.) afforded 4-[2-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-ethoxy]-benzoic acid methyl ester. 1HNMR (300 MHz, DMSO-d6) δ 8.64 (d, J=2.5 Hz, 1H), 8.39 (dd, J=2.5 & 8.9 Hz, 1H), 7.89 (d, J=8.8 Hz, 2H), 7.83 (d, J=8.9 Hz, 1H), 7.06 (d, J=8.8 Hz, 2H), 4.76 (m, 2H), 4.46 (m, 2H), 3.80 (s, 3H, OCH3). MS-EI m/z 449 [M+].

Sources & evidence

ORD record
ord-592e93e4db8e429582df75326669c211
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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