Water → HCID 22173111, compound

HRID 2298468Notes

Reaction equation

HRID 2298468 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:21]3[C:22]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:18]=[CH:19][CH:20]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 158697837-Bromo-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 22173111HCID 22173111, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Using a method similar to Example 15a), 56.3 g (0.25 mol) of 7-bromo-2-methyl-1-indanone (2), 47.3 g (0.275 mol) of 1-naphthylboronic acid and 58 g (0.55 mol) of sodium carbonate were placed in 950 ml of dimethoxyethane and 300 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 560 mg (2.5 mmol) of palladium acetate and 1.31 g (5 mmol) of triphenylphosphine (TPP) were added and the reaction mixture was stirred for 2 hours at 80° C. After addition of 700 ml of water, the mixture was extracted 5 times with 300 ml each time of diethyl ether, the ether phase was washed twice with 300 ml each time of water and with 300 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 63.3 g of (16) as solid.

Workup

  1. custom300 ml of water in the reaction vessel, the mixture was degassed a number of times
  2. extractionthe mixture was extracted 5 times with 300 ml each time of diethyl ether
  3. washthe ether phase was washed twice with 300 ml each time of water and with 300 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-74828087904048c4a815741f2e6b6c2d
Source dataset
uspto-grants-2002_12
Patent number
US06492539B1

Reaction notes

Loading…