Water → HCID 9808463, compound

HRID 1358743Notes

Reaction equation

HRID 1358743 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:13][C:14]([F:26])([F:25])[S:15]([C:18]1[CH:23]=[CH:22][C:21](Cl)=[CH:20][CH:19]=1)(=[O:17])=[O:16].C(=O)([O-])[O-].[K+].[K+].[OH2:33]>CN(C=O)C>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([O:1][C:21]2[CH:22]=[CH:23][C:18]([S:15]([C:14]([F:26])([F:25])[F:13])(=[O:17])=[O:16])=[CH:19][CH:20]=2)[CH:11]=[C:10]([O:12][C:21]2[CH:20]=[CH:19][C:18]([S:15]([C:14]([F:26])([F:13])[F:25])(=[O:16])=[O:33])=[CH:23][CH:22]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 7033241-Chloro-4-(trifluoromethylsulfonyl)benzene

Product 1

HCID 9808463HCID 9808463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 3,5-dihydroxybenzoate (100 mg, 0.595 mmol), 4-(trifluoromethylsulfonyl)chlorobenzene (291 mg, 2 equiv.) and potassium carbonate (330 mg, 4 equiv.) in DMF was heated to 100° C. overnight. The reaction was poured into water, extracted with EtOAc, washed the organic layer with water, brine, dried and concentrate. The residue was column chromatographed (1:2 EtOAc: Hex) to give 3,5-bis-(4-trifluoromethanesulfonyl-phenoxy)-benzoic acid methyl ester. 1HNMR (360 MHz, DMSO-d6) δ 8.12 (d, J=7.86 Hz, 4H), 7.67 (d, J=2.17 Hz, 2H), 7.61 (t, J=2.17 Hz, 1H), 7.42 (d, J=7.86 Hz, 4H), 3.85 (s, 3H, OCH3).

Workup

  1. extractionextracted with EtOAc
  2. washwashed the organic layer with water, brine
  3. customdried
  4. concentrationconcentrate
  5. customchromatographed (1:2 EtOAc: Hex)

Sources & evidence

ORD record
ord-750806d1603a4b9582290b47a3747950
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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