Water → 3-Fluoro-6-methoxy-9H-xanthen-9-one

HRID 425291Notes

Reaction equation

HRID 425291 reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[OH:25])=[O:16].O>CN(C)C=O>[F:14][C:12]1[CH:13]=[CH:8][C:9]2[C:15](=[O:16])[C:17]3[C:18]([O:25][C:10]=2[CH:11]=1)=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 57839205(2,4-Difluorophenyl)(2-hydroxy-4-methoxyphenyl)methanone

Product 1

HCID 578391983-Fluoro-6-methoxy-9H-xanthen-9-oneYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of potassium carbonate (2.13 g, 15.4 mmol) and (2,4-difluoro-phenyl)-(2-hydroxy-4-methoxy-phenyl)-methanone (3.4 g, 12.9 mmol) in N,N-dimethylformamide (50 mL) was heated at 100° C. for 2 h. The mixture was cooled and poured into water (˜150 mL). A solid was collected by filtration, washed with water, and dried in vacuo to give the title compound (2.8 g), which was used without purification in the subsequent step. MS: m/z 244.9 (MH+). 1H NMR (CDCl3): δ 3.94 (s, 1H), 6.88 (d, 1H, J=2.4 Hz), 6.96 (d of d, 1H, J=2.4 & 8.9 Hz), 7.07 (m, 2H), 8.24 (d, 1H, 8.9 Hz) and 8.34 (d of d, 1H, J=6.5 & 8.8 Hz).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationA solid was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6e647f29be8d4e76bd03877bbca86610
Source dataset
uspto-grants-2012_01
Patent number
US08106207B2

Reaction notes

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