Methanone, bis(5-fluoro-2,4-dihydroxyphenyl)- → 2,7-Difluoro-3,6-dihydroxyxanthone

HRID 2357123Notes

Reaction equation

HRID 2357123 reaction equation
[F:1][C:2]1[C:3]([OH:20])=[CH:4][C:5]([OH:19])=[C:6]([CH:18]=1)[C:7]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([OH:16])=[CH:11][C:10]=1O)=[O:8]>O>[F:1][C:2]1[C:3]([OH:20])=[CH:4][C:5]2[O:19][C:10]3[C:9](=[CH:14][C:13]([F:15])=[C:12]([OH:16])[CH:11]=3)[C:7](=[O:8])[C:6]=2[CH:18]=1

Participants

3

Reactant 1

HCID 12160768Methanone, bis(5-fluoro-2,4-dihydroxyphenyl)-

Product 1

HCID 121607692,7-Difluoro-3,6-dihydroxyxanthoneYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 7 (0.75 g, 2.66 mmol) was heated in a sealed tube with H2O (30 mL) at 200-220 0° C. for 2-3 h. On cooling, 2,7-difluoro-3,6-dihydroxyxanthone 8 precipitated out. The product was collected by filtration and washed with H2O to give 8 (0.58 g, 83%) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 11.4 (s, 2H), 7.67 (d, 2H, J=10.9 Hz), 6.96 (d, 2H, J=7.1 Hz); 13C NMR (75 MHz, DMSO-d6) δ 173.1, 153.1, 152.0, 151.8, 150.4, 147.2, 112.6, 112.5, 111.1, 110.8, 104.7, 104.6; 19F NMR (282 MHz, DMSO-d6) δ −139.0 (dd, 2F); mass spectrum, calculated for C13H6F2O4 (MH+) 265.0, Found 264.9.

Workup

  1. temperatureOn cooling
  2. custom2,7-difluoro-3,6-dihydroxyxanthone 8 precipitated out
  3. filtrationThe product was collected by filtration
  4. washwashed with H2O

Sources & evidence

ORD record
ord-e041736b889047928c05c77bc0662e0b
Source dataset
uspto-grants-2010_07
Patent number
US07759459B2

Reaction notes

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