Ethyl Acetate → HCID 57949465, compound

HRID 2427629Notes

Reaction equation

HRID 2427629 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.[C:14]1([CH3:23])[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[I:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:13])[N:22]([CH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH3:23])=[CH:15][CH:16]=1)[CH2:11]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 76751p-MethylphenethylamineHCID 11268261Methyl 2-(bromomethyl)-6-iodobenzoate

Product 1

HCID 57949465HCID 57949465, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.107 g, 0.3 mmol), 2-p-tolyl-ethylamine (0.072 mL, 0.5 mmol), and K2CO3 (0.083 g, 0.6 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-iodo-2-(2-p-tolyl-ethyl)-2,3-dihydro-isoindol-1-one (0.060 g, 53%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.28 (s, 3H), 2.94 (t, 2H), 3.81 (t, 2H), 4.76 (s, 2H), 7.12-7.36 (m, 6H), 7.86 (d, 1H). GC-MS: m/z 377 (M)+, 272(M−105)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-2c38d5fc671541c3a7e9898ef5955976
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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