Boronic Acid → HCID 68888072, compound

HRID 1432343Notes

Reaction equation

HRID 1432343 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:37]2[CH2:42][CH2:41]CCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:41]1([C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][C:9]3=[O:12])=[CH:4][CH:3]=2)[CH2:42][CH2:37]1

Participants

8

Reactant 4

HCID 61668Boronic AcidHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 68888072HCID 68888072, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a yellow suspension of 2 g 7-Bromo-1-tetralone, 1 g boronic acid, 7.1 g potassium phosphate (pulverized) and 0.28 g tricyclohexylphosphine in 40 ml toluene and 2 ml water 0.1 g of palladium acetate is added under a argon atmosphere. The mixture is heated to 100° C. After 1 h, the reaction mixture is allowed to cool to rt and quenched with water. The reaction mixture is extracted with EtOAc. The combined organic phases are washed with brine, dried over sodium sulfate and filtered. The brown oil is purified by flash-chromatography (hexane/EtOAc=6/1).

Workup

  1. additionis added under a argon atmosphere
  2. temperatureto cool to rt
  3. customquenched with water
  4. extractionThe reaction mixture is extracted with EtOAc
  5. washThe combined organic phases are washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe brown oil is purified by flash-chromatography (hexane/EtOAc=6/1)

Sources & evidence

ORD record
ord-c1c5b95165c94bddb3bf522736e76e29
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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