Potassium Iodide → HCID 21187923, compound

HRID 1870418Notes

Reaction equation

HRID 1870418 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][CH:24]1[CH2:27][C:26](F)(F)[C:25]1([F:31])[F:30]>CN(C)C=O.O.C(OCC)C>[F:30][C:25]1([F:31])[C:26]([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])=[CH:27][C:24]1=[CH2:23]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27822713-(Chloromethyl)-1,1,2,2-tetrafluorocyclobutaneHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 21187923HCID 21187923, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A stirred solution of methyl 3-hydroxy-4-methoxybenzoate (1.72 g), potassium iodide (0.1 g), and potassium carbonate (1.55 g) in dimethylformamide (50 mL) is treated with 1-chloromethyl-2,2,3,3-tetrafluorocyclobutane (2.0 g), and the solution is stirred at 70-80° C. for 6 hours. After cooling, the reaction mixture is diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The organic extracts are combined, dried over magnesium sulfate and concentrated, to give a golden oil. The oil is subjected to flash chromatography, using diethyl ether as eluent, to give methyl 3-(4,4-difluoro-3-methylenecyclobut-1-enyloxy)-4-methoxybenzoate, m.p. 60-62° C. [Elemental analysis: C,59.5; H,4.3%; calculated: C,52.2; H,4.4%].

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a golden oil

Sources & evidence

ORD record
ord-ca3ce8a93d854820b9aebdf9d930cc53
Source dataset
uspto-grants-2000_08
Patent number
US06096768

Reaction notes

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