Ethyl Acetate → HCID 57949727, compound

HRID 2427617Notes

Reaction equation

HRID 2427617 reaction equation
CO[C:3](=[O:13])[C:4]1[C:9]([I:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:20]2[CH2:11][C:5]3[C:4](=[C:9]([I:10])[CH:8]=[CH:7][CH:6]=3)[C:3]2=[O:13])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 660364-ChlorobenzylamineHCID 11268261Methyl 2-(bromomethyl)-6-iodobenzoate

Product 1

HCID 57949727HCID 57949727, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.200 g, 0.56 mmol), 4-chloro-benzylamine (0.7 mmol), and K2CO3 (0.166 g, 1.2 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(4-chloro-benzyl)-7-iodo-2,3-dihydro-isoindol-1-one (0.084 g, 39%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.16 (s, 2H), 4.75 (s, 2H), 7.16-7.40 (m, 6H), 7.92 (d, 1H). GC-MS: m/z 367 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-103cedd473b84096a8bab38fc8112d42
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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