2,2,2-Trifluoroethanol → HCID 67251522, compound

HRID 2427743Notes

Reaction equation

HRID 2427743 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[C:7](=[O:12])[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)[CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[F:27][C:28]([F:32])([F:31])[CH2:29][OH:30]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C>[F:27][C:28]([F:32])([F:31])[CH2:29][O:30][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[C:7](=[O:12])[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)[CH2:5]2

Participants

7

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 67251198HCID 67251198, compound

Product 1

HCID 67251522HCID 67251522, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5,7-dichloro-2-(4-bromo-benzyl)-2,3-dihydro-isoindol-1-one (0.148 g, 0.4 mmol), palladium(II) acetate (0.004 g, 0.02 mmol), rac-2-(di-t-butylphosphino)-1,1′-binaphthyl (0.009 g, 0.025 mmol), and cesium carbonate (0.228 g, 0.7 mmol) in toluene (5 mL) was treated with 2,2,2-trifluoro ethanol (0.082 μL, 0.8 mmol) and stirred at 110° C. for 12 h. After this time the solvent was evaporated and silica gel column chromatography using, typically 30% ethyl acetate in hexane, afforded the desired product (0.110 g, 64%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.02 (s, 2H), 4.53 (m, 4H), 6.86 (s, 1H), 6.91 (s, 1H), 6.93 (d, 2H), 7.37 (d, 2H). GC-MS: m/z 435 (M)+.

Workup

  1. customAfter this time the solvent was evaporated

Sources & evidence

ORD record
ord-b297efe9ff704657a9eaf132db0d9315
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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