Acetic Acid → HCID 11528980, compound

HRID 418825Notes

Reaction equation

HRID 418825 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][C:12]3[C:17]([C:18](=[O:20])[CH:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:6][C:7]=1[O:8]C.CC(O)=O.O>I>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][C:12]3[C:17]([C:18](=[O:20])[CH:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 66553888HCID 66553888, compound

Product 1

HCID 11528980HCID 11528980, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2′-hydroxyacetophenone (1.36 g, 10 mmol) in 20 mL anhydrous pyridine was added 3-fluoro-4-methoxybenzoyl chloride (1.89 g, 10 mmol) and the reaction mixture was stirred at rt for 15 h under a nitrogen atmosphere. The reaction mixture was poured into 200 mL of 2 N HCl. The formed solid was isolated by filtration, washed with water and dried under vacuum to give a white solid (2.76 g, 95.7%). The compound (2.68 g, 9.3 mmol) was dissolved in 10 mL anhydrous pyridine. Powdered potassium hydroxide (1.57 g, 27.9 mmol) was added and the reaction mixture was stirred at rt overnight under nitrogen. Water (100 mL) was added, the solid was isolated by filtration and washed with water to give a yellow solid (1.83 g, 68%). The compound (1.78 g, 6.17 mmol) was suspended in 15 mL glacial AcOH. Five drops of conc. HCl was added and the reaction mixture was stirred at 110° C. for 2 h, then cooled to rt. Water (100 mL) was added. The formed solid was separated by filtration, washed with water and dried under vacuum to give 2-(3-fluoro-4-methoxyphenyl)chromen-4-one as a white solid (1.62 g, 97%). 2-(3-Fluoro-4-methoxyphenyl)chromen-4-one (1.6 g, 5.92 mmol) was suspended in 40 mL of HI. Glacial AcOH (15 mL) was added and the reaction mixture was stirred at 110° C. for 4 h, then cooled to rt. Water (200 mL) was added, and the solid was isolated by filtration, washed with water and dried under vacuum. The crude compound was washed with 1:1 dichloromethane and methanol (15 mL) to give 1.1 g of 2-(3-fluoro-4-hydroxyphenyl)chromen-4-one (72%) as a pale yellow solid. MS (ES) m/z: 257.91 (M+1), 256.88 (M); Mp. 275-276° C.

Workup

  1. temperaturecooled to rt
  2. customthe solid was isolated by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. washThe crude compound was washed with 1:1 dichloromethane and methanol (15 mL)

Sources & evidence

ORD record
ord-593b08af6ad24295ac14d325167ffd8a
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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