Hydrochloric Acid → [3,5-Bis-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-phenyl]-acetic acid methyl ester

HRID 1358744Notes

Reaction equation

HRID 1358744 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.[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].Cl>C1COCC1>[CH3:13][O:12][C:10](=[O:11])[CH2:9][C:4]1[CH:3]=[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:7]=[C:6]([O:8][C:20]2[CH:21]=[CH:22][C:23]([S:25]([C:28]([F:30])([F:31])[F:29])(=[O:27])=[O:26])=[CH:24][C:19]=2[N+:16]([O-:18])=[O:17])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 579787Methyl 3,5-dihydroxyphenylacetateHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzene

Product 1

HCID 9831429[3,5-Bis-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-phenyl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3,5-dihydroxyphenylacetate (50 mg, 0.274 mmol) in THF at rt was added NaH (24 mg, 60% dispersion in mineral oil), followed by 2-nitro-4-(trifluoromethylsulfonyl)chlorobenzene (159 mg, 2 equiv.). The mixture was stirred at rt for 5 hr. The reaction was acidified with 2N HCl, extracted into EtOAc, washed with water, brine, dried and concentrated. The residue was column chromatographed (EtOAc: Hex) to give [3,5-bis-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-phenyl]-acetic acid methyl ester. 1HNMR (360 MHz, DMSO-d6) δ 8.77 (d, J=2.3 Hz, 2H), 8.33 (dd, J=2.3 & 8.9 Hz, 2H), 7.46 (d, J=8.9 Hz, 2H), 7.40 (t, J=2.4 Hz, 1H), 7.30 (d, J=2.4 Hz, 2H), 3.89 (s, 2H, CH2), 3.63 (s, 3H, OCH3). MS-EI m/z 688 [M+].

Workup

  1. extractionextracted into EtOAc
  2. washwashed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed (EtOAc: Hex)

Sources & evidence

ORD record
ord-d1d7547fbdb14f81a40bac0e90c21cbb
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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