Ethyl Acetate → HCID 11710585, compound

HRID 2427627Notes

Reaction equation

HRID 2427627 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.[CH2:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1)[CH3:15].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:21]([CH2:20][C:19]1[CH:22]=[CH:23][C:16]([CH2:14][CH3:15])=[CH:17][CH:18]=1)[CH2:11]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 38702194-ethylbenzylamineHCID 11268261Methyl 2-(bromomethyl)-6-iodobenzoate

Product 1

HCID 11710585HCID 11710585, compoundYield 28.3%

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), 4-ethyl-benzylamine (0.072 mL, 0.5 mmol), and K2CO3 (0.138 g, 1.0 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 7-iodo-2-(4-ethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.032 g, 28%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.24 (t, 3H), 2.51 (q, 2H), 4.14 (s, 2H), 4.76 (s, 2H), 7.14-7.38 (m, 6H), 7.86 (d, 1H). GC-MS: m/z 377 (M)+, 348 (M−29)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-207b2e12f2754bad83e9446b9eea8c81
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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