Ethanol → HCID 23113834, compound

HRID 1787181Notes

Reaction equation

HRID 1787181 reaction equation
FC(F)(F)S(O[C:7]1[C:11]2[C:12]([CH3:19])=[C:13]([Br:18])[C:14]([CH3:17])=[C:15]([CH3:16])[C:10]=2[O:9][CH:8]=1)(=O)=O.[CH2:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)[CH3:23].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>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.O.C1(C)C=CC=CC=1>[Br:18][C:13]1[C:14]([CH3:17])=[C:15]([CH3:16])[C:10]2[O:9][CH:8]=[C:7]([C:27]3[CH:28]=[CH:29][C:24]([CH2:22][CH3:23])=[CH:25][CH:26]=3)[C:11]=2[C:12]=1[CH3:19]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734352Boronic acid, (4-ethylphenyl)-HCID 23114222HCID 23114222, compound

Product 1

HCID 23113834HCID 23113834, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixed solution of 5-bromo-4,6,7-trimethyl-1-benzofuran-3-yl trifluoromethanesulfonate obtained in Reference Example 261 (1.35 g, 3.49 mmol), 4-ethylphenyl boronic acid (523 mg, 3.49 mmol), tetrakis(triphenylphosphine)palladium(0) (81 mg, 0.07 mmol) in a 2 N aqueous sodium carbonate solution (4 mL)-ethanol (4 mL)-toluene (15 mL) was reacted under argon atmosphere at 80° C. for 5 hours. Water was added to the reaction solution, which was extracted with ethyl acetate. The combined organic layer was washed with a saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, the residue was purified by silica gel column chromatography (hexane) to obtain 1.10 g (yield 92%) of the title compound. Oily matter.

Workup

  1. customwas reacted under argon atmosphere at 80° C. for 5 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic layer was washed with a saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-e41f759fb0f443a087884c5e0daabf11
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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