Ethyl Acetate → (S)-5,7-dichloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one

HRID 2427751Notes

Reaction equation

HRID 2427751 reaction equation
CO[C:3](=[O:14])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[CH2:12]Br.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]([NH2:24])[CH3:23])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Cl:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([Cl:10])[CH:8]=1)[C:3](=[O:14])[N:24]([C@H:22]([C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1)[CH3:23])[CH2:12]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1550852(S)-(-)-1-(4-chlorophenyl)ethylamineHCID 579493492-Bromomethyl-4,6-dichlorobenzoic acid methyl ester

Product 1

HCID 57949800(S)-5,7-dichloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-oneYield 35%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-Bromomethyl-4,6-dichloro-benzoic acid methyl ester (0.119 g, 0.4 mmol), (S)-1-(4-chloro-phenyl)-ethyl amine (0.067 mL, 0.48 mmol), and K2CO3 (0.104 g, 0.8 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography of the product using 30% ethyl acetate in hexane afforded (S)-5,7-dichloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (0.047 g, 35%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.64 (d, 3H), 3.94 (d, 1H), 4.26 (d, 1H), 5.74 (q, 1H) 7.22-7.42 (m, 6H). GC-MS: m/z 340 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-ad45390c1a4445a08017dbe1bd817914
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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