Water → HCID 22173022, compound

HRID 2298486Notes

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.[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([F:20])[CH:19]=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:16]3[CH:15]=[C:14]([F:13])[CH:19]=[C:18]([F:20])[CH:17]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

2.25 g (0.01 mol) of 7-bromo-2-methyl-1-indanone (2), 1.74 g (0.011 mol) of 3,5-difluorophenylboronic acid and 2.33 g (0.022 mol) of sodium carbonate were placed in 38 ml of dimethoxyethane and 12 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 45 mg (0.2 mmol) of palladium acetate and 0.1 g (0.4 mmol) of triphenylphosphine (TPP) were added and the reaction mixture was stirred for 2 hours at 80° C. After addition of 50 ml of water, the mixture was extracted 3 times with 30 ml each time of diethyl ether, the ether phase was washed twice with water and dried over magnesium sulfate. Removal of the solvent gave 2.4 g of 2-methyl-7-(3,5-difluorophenyl)-1-indanone as solid.

Workup

custom12 ml of water in the reaction vessel, the mixture was degassed a number of times
extractionthe mixture was extracted 3 times with 30 ml each time of diethyl ether
washthe ether phase was washed twice with water
dry with materialdried over magnesium sulfate
customRemoval of the solvent

Sources & evidence

ORD record: ord-4f39af4bb2bf440b81d56359d78bdc21
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492539B1

Reaction notes

Loading…