Hydrochloric Acid → HCID 21947847, compound

HRID 2215156Notes

Reaction equation

HRID 2215156 reaction equation
Br[C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:13][CH3:14])[CH:3]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Cl>O1CCOCC1.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>[CH3:12][O:11][C:10]1[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]([O:13][CH3:14])=[CH:3][C:2]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([F:27])([F:26])[F:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 219477224-Bromo-2,5-dimethoxybenzoic acid

Product 1

HCID 21947847HCID 21947847, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 4-bromo-2,5-dimethoxybenzoic acid [prepared in the manner of Bortnik et al., Zh. Org. Khim. 8, 340 (1972)] (2.43g, 9 mmol), 2-trifluoromethylphenyl boronic acid (5.3 g, 28 mmol), and potassium carbonate (6.21 g, 60 mmol) in dioxane (40 mL) was sparged with nitrogen and treated with tetrakis(triphenylphosphine)palladium(0) (0.328 g, 0.2 mmol). The mixture was heated to reflux for 48 hours, cooled, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extracts were dried over anhydrous magnesium sulfate, filtered and stripped to a solid which was used as such in the next step.

Workup

  1. customprepared in the manner of Bortnik et al., Zh
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 48 hours
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-04af378baf6a402eaecd5bf44a50e800
Source dataset
uspto-grants-2006_09
Patent number
US07109193B2

Reaction notes

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