Ethyl Acetate → 7-Chloro-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427606Notes

Reaction equation

HRID 2427606 reaction equation
CO[C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.[O:14]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Cl:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:13])[N:26]([CH2:25][C:24]1[CH:27]=[CH:28][C:21]([O:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:22][CH:23]=1)[CH2:11]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2760343(4-Phenoxyphenyl)methanamineHCID 22935208Methyl 2-(bromomethyl)-6-chlorobenzoate

Product 1

HCID 115593517-Chloro-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-oneYield 34.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-6-chloro-benzoic acid methyl ester (0.132 g, 0.5 mmol), 4-phenoxy benzylamine (0.124 g, 0.7 mmol), and K2CO3 (0.152 g, 1.1 mmol) in toluene (4 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-chloro-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.06 g, 34%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.24 (s, 2H), 4.76 (s, 2H), 6.98-7.46 (m, 12H). GC-MS: m/z 349 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-b718eed674694f50b20771ec137431e4
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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