Toluene → HCID 69420577, compound

HRID 457541Notes

Reaction equation

HRID 457541 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16](Br)[CH:15]=2)[C:7]=1[F:23])[CH3:2].[C:25]1(C)C=CC=C[CH:26]=1.C(C([Sn])=C(CCCC)CCCC)CCC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][C:14]2[CH:15]=[C:16]([CH:25]=[CH2:26])[CH:17]=[C:18]([C:20]#[N:21])[CH:19]=2)[C:7]=1[F:23])[CH3:2]

Participants

6

Reactant 3

HCID 1140TolueneHCID 53438229Tri(butyl)vinyltinHCID 66999437HCID 66999437, compound

Product 1

HCID 69420577HCID 69420577, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 2-necked flask was equipped with a reflux condenser and charged with 117c (1.14 g, 2.78 mmol) and tetrakis(triphenylphosphine)palladium (308 mg, 0.28 mmol). Anhydrous toluene (15 mL) and tributylvinyltin (0.85 mL, 2.91 mmol) were added, and the reaction was heated to reflux under nitrogen for 16 h. The solution was cooled to RT and EtOAc (50 mL) was added. The mixture was washed with H2O (25 mL) and brine (25 mL), and dried over anhydrous MgSO4. The solvents were evaporated, and the resulting oil purified by flash chromatography over silica gel(0% to 25% EtOAc/hexanes) to provide 770 mg (78%) of [4-chloro-3-(3-cyano-5-vinyl-phenoxy)-2-fluoro-phenyl]-acetic acid ethyl ester (118).

Workup

  1. customA 2-necked flask was equipped with a reflux condenser
  2. temperaturethe reaction was heated
  3. temperatureto reflux under nitrogen for 16 h
  4. washThe mixture was washed with H2O (25 mL) and brine (25 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvents were evaporated
  7. customthe resulting oil purified by flash chromatography over silica gel(0% to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-748086326eed4e4db1f0ac55a7024f2e
Source dataset
uspto-grants-2007_03
Patent number
US07189718B2

Reaction notes

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