Phthalimidine → 2-(4-Trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427569Notes

Reaction equation

HRID 2427569 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.CCCCCC.C(OCC)(=O)C>[F:21][C:20]([F:22])([F:23])[O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:10])=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 10199PhthalimidineHCID 10796Cesium carbonateHCID 2855718-Crown-6HCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 579496892-(4-Trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneYield 81%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,3-dihydro-isoindol-1-one (0.133 g, 1 mmol), 1-bromomethyl-4-trifluoromethoxy-benzene (0.306 g, 1.2 mmol), Cs2CO3 (0.816 g, 2.5 mmol), and 18-crown-6 (0.026 g, 0.1 mmol) in acetone (5 mL) was stirred at 70° C. for 16 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.125 g, 81%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.28 (s, 2H), 4.82 (s, 2H), 7.16 (d, 2H), 7.32-7.52 (m, 5H), 7.90 (d, 1H).

Sources & evidence

ORD record
ord-c1097711188b469c949d21e765748648
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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