3-Formylphenylboronic acid → HCID 23157556, compound

HRID 507973Notes

Reaction equation

HRID 507973 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10](Br)=[C:9]([CH3:15])[CH:8]=1)[CH3:2].[CH:16]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)=[O:17]>C(=O)([O-])[O-].[Na+].[Na+].C(O)C.C1(C)C=CC=CC=1.[Cl-].[Na+].O.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>[CH2:1]([O:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:16]=[O:17])[CH:23]=2)=[C:9]([CH3:15])[CH:8]=1)[CH3:2]

Participants

8

Reactant 2

HCID 27343563-Formylphenylboronic acidHCID 23157240HCID 23157240, compound

Product 1

HCID 23157556HCID 23157556, compoundYield 38.2%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

2-[(4-Bromo-3,5-dimethylphenyl)thio]ethyl ethyl ether (2.41 g, 8.33 mmol) and (3-formylphenyl)boronic acid (1.37 g, 9.16 mmol) were dissolved in a mixture of 2 M aqueous sodium carbonate solution (24 mL), ethanol (8 mL) and toluene (24 mL), the air was substituted with argon gas, and tetrakis(triphenylphosphine)palladium(0) (0.48 g, 0.42 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 16 hr. After cooling the reaction mixture, saturated brine was added and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=5/1) to give the title compound (1.00 g, yield 38%) as a colorless oil.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture was extracted with diethyl ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-95ba8aa4a29340d2bf67df53044e853d
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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