Water → 4-[3-(4-Trifluoromethanesulfonyl-phenoxy)-phenoxy]-benzoic acid

HRID 1358751Notes

Reaction equation

HRID 1358751 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.[F:18][C:19]([F:31])([F:30])[S:20]([C:23]1[CH:28]=[CH:27][C:26](Cl)=[CH:25][CH:24]=1)(=[O:22])=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:30][C:19]([F:18])([F:31])[S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:1][C:2]2[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=2)[O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=2)=[CH:25][CH:24]=1)(=[O:21])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6153894-(3-Hydroxyphenoxy)benzoic acidHCID 7033241-Chloro-4-(trifluoromethylsulfonyl)benzene

Product 1

HCID 98459634-[3-(4-Trifluoromethanesulfonyl-phenoxy)-phenoxy]-benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(3-hydroxyphenoxy)benzoic acid (100 mg, 0.434 mmol), 4-(trifluoromethylsulfonyl)chlorobenzene (106 mg, 1 equiv.) and potassium carbonate (240 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 concentrated. The residue was column chromatographed to give 4-[3-(4-trifluoromethanesulfonyl-phenoxy)-phenoxy]-benzoic acid. 1HNMR (300 MHz, DMSO-d6) δ 8.09 (d, J=8.97 Hz, 2H), 7.95 (d, J=8.94 Hz, 2H), 7.56 (t, J=8.54 Hz, 1H), 7.33 (d, J=8.94 Hz, 2H), 7.10 (d, J=8.97 Hz, 2H), 7.04-7.11 (m, 3H). MS-EI m/z 438 [M+].

Workup

  1. extractionextracted with EtOAc
  2. washwashed the organic layer with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-86a54f0463a44c3b9d31b9166ab81ecf
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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