Phenylboronic Acid → HCID 22556974, compound

HRID 983805Notes

Reaction equation

HRID 983805 reaction equation
Br[C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH:5]=[O:6].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CCOCC.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>[OH:11][C:3]1[C:4]([CH:5]=[O:6])=[CH:7][C:8]([CH3:10])=[CH:9][C:2]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 2

HCID 66827Phenylboronic AcidHCID 27570153-bromo-2-hydroxy-5-methylbenzaldehyde

Product 1

HCID 22556974HCID 22556974, compoundYield 50.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-2-hydroxy-5-methylbenzaldehyde (0.30 g, 1.40 mmoles), phenyl boronic acid (0.20 g, 1.67 mmoles) and tetrakis(triphenylphosphine)palladium(0) (81 mg, 0.07 mmoles) in toluene (10 ml) and 2M K2CO3 (3 ml) was heated to 80° C. for 2 hr. The reaction mixture was cooled to ambient temperature, diluted with ether (100 ml) and washed with NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated to yield a residue which was purified using flash chromatography (10% ethyl acetate/hexanes) to yield 0.15 g (49%) of the title compound as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washwashed with NaHCO3
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a residue which
  7. customwas purified

Sources & evidence

ORD record
ord-cf82e8c79a044ef2bbf0875d9021a4bf
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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