HCID 90038965, compound → HCID 90039503, compound

HRID 2207326Notes

Reaction equation

HRID 2207326 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]#[C:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1>O>[F:10][C:8]1[CH:9]=[C:4]2[C:5]([CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[O:2][C:3]2=[O:20])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 90038965HCID 90038965, compound

Product 1

HCID 90039503HCID 90039503, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-fluoro-2-p-tolylethynyl-benzoic acid methyl ester (359 mg, 1.34 mmol) and polyphosphoric acid (4 g) is heated to 80° C. and stirred at this temperature for 20 hours. The reaction mixture is allowed to cool to room temperature and water is added. The mixture is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/dichloromethane as eluent to afford 7-fluoro-3-p-tolyl-isochromen-1-one as off-white solid; HPLC/MS 2.16 min (A), [M+H] 255.

Workup

  1. temperatureto cool to room temperature
  2. customThe mixture is partitioned between water and dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on a silica gel column with cyclohexane/dichloromethane as eluent

Sources & evidence

ORD record
ord-457b4356af364c1e8cb0103cb0285125
Source dataset
uspto-grants-2016_06
Patent number
US09376433B2

Reaction notes

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