Potassium Phosphate, Tribasic → HCID 90786971, compound

HRID 72252Notes

Reaction equation

HRID 72252 reaction equation
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:9])[CH2:3][C:2]2=[O:10].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:54]1[CH:55]=[C:56]([C:62]2[CH:67]=[CH:66][C:65]([Cl:68])=[CH:64][CH:63]=2)[CH:57]=[CH:58][C:59]=1[CH2:60][CH3:61]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:68][C:65]1[CH:66]=[CH:67][C:62]([C:56]2[CH:55]=[CH:54][C:59]([CH2:60][CH3:61])=[C:58]([CH:3]3[C:4](=[O:9])[CH:5]4[CH2:8][CH:1]([CH2:7][CH2:6]4)[C:2]3=[O:10])[CH:57]=2)=[CH:63][CH:64]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 144686Bicyclo(3.2.1)octane-2,4-dioneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 594459053-Bromo-4'-chloro-4-ethylbiphenyl

Product 1

HCID 90786971HCID 90786971, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
160 °C

Procedure

To a microwave vial containing bicyclo[3.2.1]octane-2,4-dione (0.112 g, 0.812 mmol), palladium (II) acetate (7.6 mg, 0.034 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (24.2 mg, 0.051 mmol), and finely ground potassium phosphate (0.316 g, 1.49 mmol) is added degassed dimethoxyethane (2 ml), then 3-bromo-4′-chloro-4-ethylbiphenyl (0.200 g, 0.667 mmol). This reaction mixture is then heated at 160° C. under microwave irradiation for 60 minutes, then cooled to room temperature and washed with 2M hydrochloric acid (2 ml) and extracted with ethyl acetate (3×3 ml). The organic phase is dried over magnesium sulfate, filtered, and the filtrate concentrated in vacuo. The crude mixture is purified by flash column chromatography on silica gel (30% to 100% ethyl acetate/hexane eluant ratio) to afford 3-(4′-chloro-4-ethylbiphen-3-yl)bicyclo[3.2.1]octane-2,4-dione.

Workup

  1. additionis added
  2. customdegassed dimethoxyethane (2 ml)
  3. temperaturecooled to room temperature
  4. washwashed with 2M hydrochloric acid (2 ml)
  5. extractionextracted with ethyl acetate (3×3 ml)
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customThe crude mixture is purified by flash column chromatography on silica gel (30% to 100% ethyl acetate/hexane eluant ratio)

Sources & evidence

ORD record
ord-92a1ccd6de8244509b812042a867396c
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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