Boric Acid → Propiophenone, 4'-phenyl-

HRID 1591790Notes

Reaction equation

HRID 1591790 reaction equation
[C:1]1(OB(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][CH3:20])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].B(O)(O)O>O.[Pd](Cl)Cl.C(OCC)(=O)C>[C:12]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][CH3:20])=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 7628Boric AcidHCID 10340Sodium CarbonateHCID 66312p-BromopropiophenoneHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 95230Propiophenone, 4'-phenyl-

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture containing phenylboric acid (6.1 g; 50 mmol), 4′-bromopropiophenone (10.65 g; 50 mmol), sodium carbonate (5.3 g; 50 mmol) and palladium chloride (500 mg, 2.8 mmol) in 300 ml of water is heated under reflux for 4 hours. Boric acid (1 g; 0.8 mmol) is then added followed by heating for 30 minutes. Once the mixture has been returned to 23° C., 250 ml of ethyl acetate is added followed by filtering on frit then on GFA paper. The filtrate is decanted and the organic phase is washed with a saturated solution of NaCl before being dried over MgSO4 and concentrated using a rotary evaporator. The precipitate is stirred for 30 minutes in 100 ml of isopentane and 5 ml of dichloromethane. After filtration on frit, the solid is rinsed with isopentane. A cream coloured powder is obtained (8.7 g; 83%). Melting point: 98-99° C. MH+=211.1

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. temperatureby heating for 30 minutes
  4. customhas been returned to 23° C.
  5. filtrationby filtering on frit
  6. customThe filtrate is decanted
  7. washthe organic phase is washed with a saturated solution of NaCl
  8. dry with materialbefore being dried over MgSO4
  9. concentrationconcentrated
  10. customa rotary evaporator
  11. filtrationAfter filtration on frit
  12. washthe solid is rinsed with isopentane
  13. customis obtained (8.7 g; 83%)

Sources & evidence

ORD record
ord-bce2ed3a27c24dc2b58ae2d29b494c26
Source dataset
uspto-grants-2007_11
Patent number
US07291641B2

Reaction notes

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