Potassium Carbonate → HCID 89648201, compound

HRID 1773965Notes

Reaction equation

HRID 1773965 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3]I.[CH2:7]([O:9][C:10](=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([Br:19])[CH:13]=1)[CH3:8].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)Cl.O>[CH2:7]([O:9][C:10](=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:3][C:2]([F:6])([F:5])[F:1])=[C:14]([Br:19])[CH:13]=1)[CH3:8]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 18620106Ethyl 2-(3-bromo-4-hydroxyphenyl)acetate

Product 1

HCID 89648201HCID 89648201, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

1,1,1-Trifluoro-2-iodoethane (0.15 mL, 1.5 mmol, 1 eq.) was added to a solution of (3-bromo-4-hydroxy-phenyl)-acetic acid ethyl ester (456 mg, 1.5 mmol, 1 eq.) and potassium carbonate (622 mg, 4.5 mmol, 3 eq.) in DMF (1.5 mL). The resulting mixture was stirred at 150° C. under microwave irradiation for 30 min. The reaction mixture was diluted with DCM and water. The layers were separated and the aq. phase was extracted with DCM (2×). The comb. org. layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flashmaster (column: 50 g, flow: 30 mL/min, 30 fractions of 30 mL, Heptane 100% to Heptane+AcOEt 20%) to yield the title compound as a colorless oil.

Workup

  1. customThe layers were separated
  2. extractionthe aq. phase was extracted with DCM (2×)
  3. dry with materiallayers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flashmaster (column: 50 g, flow: 30 mL/min, 30 fractions of 30 mL, Heptane 100% to Heptane+AcOEt 20%)

Sources & evidence

ORD record
ord-86205ed650084b298130012bda3511d0
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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