Phenylboronic Acid → HCID 59707359, compound

HRID 1422866Notes

Reaction equation

HRID 1422866 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8](Br)[C:7]([O:11][CH2:12][O:13][CH3:14])=[CH:6][C:5]=1[O:15][CH2:16][O:17][CH3:18].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]([O:11][CH2:12][O:13][CH3:14])=[CH:6][C:5]=1[O:15][CH2:16][O:17][CH3:18])=[O:19]

Participants

6

Reactant 4

HCID 66827Phenylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 59707361HCID 59707361, compound

Product 1

HCID 59707359HCID 59707359, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A Schlenk tube was charged with 5-bromo-2,4-bis-methoxymethoxy-benzoic acid methyl ester (3) (503 mg, 1.5 mmol), penylboronic acid (272 mg, 2.3 mmol), Pd(OAc)2 (22 mg, 0.1 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (82 mg, 0.2 mmol), K3PO4 H2O (4.70 g, 34.0 mmol). The reaction tube was evacuated and backfilled with N2 (X3). Toluene (10 mL, anhydrous and sure seal bottle from Aldrich) was added. The reaction was stirred at room temperature for 10 min and heated at 105° C. (preheated oil bath) for 24 h. The reaction mixture was allowed to cool to room temperature and diluted with EtOAc (50 mL) and water (70 mL). The aqueous phase was extracted with EtOAc (40 mL×3) and the combined organic layers were washed with water and brine and dried over MgSO4. The purification of the concentrated crude product by column chromatography (25% EtOAc in Hexane) afforded the title product as colorless oil (460 mg, 93%).

Workup

  1. customThe reaction tube was evacuated
  2. additionToluene (10 mL, anhydrous and sure seal bottle from Aldrich) was added
  3. temperatureheated at 105° C. (preheated oil bath) for 24 h
  4. temperatureto cool to room temperature
  5. additiondiluted with EtOAc (50 mL) and water (70 mL)
  6. extractionThe aqueous phase was extracted with EtOAc (40 mL×3)
  7. washthe combined organic layers were washed with water and brine
  8. dry with materialdried over MgSO4
  9. customThe purification of the
  10. concentrationconcentrated crude product by column chromatography (25% EtOAc in Hexane)

Sources & evidence

ORD record
ord-1de55a7fe1084f78a2f048d22b4c8831
Source dataset
uspto-grants-2015_01
Patent number
US08927548B2

Reaction notes

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