HCID 69937938, compound → HCID 71087651, compound

HRID 1897583Notes

Reaction equation

HRID 1897583 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10](OCC)OCC)=[CH:4][C:3]=1[F:17]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([F:17])=[CH:4][C:5]2[O:8][CH:9]=[CH:10][C:6]=2[CH:7]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH:9]=[CH:10][C:4]=2[C:3]=1[F:17]

Participants

3

Reactant 1

HCID 69937938HCID 69937938, compound

Product 1

HCID 71087651HCID 71087651, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
200 °C

Procedure

To 13a (3.44 g, 13.09 mmol) in toluene (13.09 ml) at room temperature was added amberlyst 15 (700 mg, 13.09 mmol). The mixture was stirred at 200° C. for 10 min in microwave. The mixture was cooled to room temperature and then the solvent was concentrated. The residue was purified via Biotage (heptane; SNAP25 column) giving 13b (505 mg, 23%) as a colorless oil. 1H NMR of major isomer in mixture (400 MHz, MeOD) δ ppm 6.84 (dd, J=2.27, 0.95 Hz, 1H) 7.46 (dd, J=9.16, 0.95 Hz, 1H) 7.71 (d, J=7.39 Hz, 1H) 7.81 (d, J=2.27 Hz, 1H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationthe solvent was concentrated
  3. customThe residue was purified via Biotage (heptane; SNAP25 column)

Sources & evidence

ORD record
ord-25a911b13c7d4bf292b76a96af3ad4f7
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

Loading…