Sodium hydride → 4-Methyl-2,6-bis-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-benzoic acid methyl ester

HRID 1358746Notes

Reaction equation

HRID 1358746 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([OH:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[N+:16]([C:19]1[CH:24]=[C:23]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[CH:22]=[CH:21][C:20]=1Cl)([O-:18])=[O:17]>>[CH3:7][O:6][C:4](=[O:5])[C:3]1[C:2]([O:1][C:20]2[CH:21]=[CH:22][C:23]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])=[CH:24][C:19]=2[N+:16]([O-:18])=[O:17])=[CH:11][C:10]([CH3:12])=[CH:9][C:8]=1[O:13][C:20]1[CH:21]=[CH:22][C:23]([S:25]([C:28]([F:30])([F:31])[F:29])(=[O:27])=[O:26])=[CH:24][C:19]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 85612Methyl 2,6-dihydroxy-4-methylbenzoateHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzene

Product 1

HCID 99179934-Methyl-2,6-bis-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-benzoic acid methyl ester

Procedure

Using procedure as in Example 10, a reaction of methyl 2,6-dihydroxy-4-methylbenzoate (50 mg, 0.274 mmol), NaH (24 mg, 2.2 equiv.) and 2-nitro-4-(trifluoromethylsulfonyl)chlorobenzene (159 mg, 2 equiv.) afforded 4-methyl-2,6-bis-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-benzoic acid methyl ester. 1HNMR (360 MHz, DMSO-d6) δ 8.80 (d, J=2.2 Hz, 2H), 8.32 (dd, J=2.2 & 9.0 Hz, 2H), 7.48 (d, J=2.7 Hz, 2H), 7.44 (s, 2H), 3.50 (s, 3H, OCH3), 1.23 (s, 3H, CH3). MS-APCI (negative mode) m/z 686.6 [M+−2].

Sources & evidence

ORD record
ord-759f3b7cab5c4e489341100a8688d0fb
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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