Ethyl Acetate → HCID 57455233, compound

HRID 2427631Notes

Reaction equation

HRID 2427631 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.[CH3:14][O:15][C:16]1[CH:30]=[CH:29][CH:28]=[CH:27][C:17]=1[O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH2:23].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:23]([CH2:22][C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([O:18][C:17]3[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=3[O:15][CH3:14])[CH:20]=1)[CH2:11]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 3850792HCID 3850792, compoundHCID 11268261Methyl 2-(bromomethyl)-6-iodobenzoate

Product 1

HCID 57455233HCID 57455233, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.178 g, 0.5 mmol), 3-(2-methoxy-phenoxy)-benzylamine (0.160 g, 0.6 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-[3-(2-methoxy-phenoxy)-benzyl]-2,3-dihydro-isoindol-1-one (0.056 g, 24%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.82 (s, 3H), 4.16 (s, 2H), 4.74 (s, 2H), 6.84-7.40 (m, 10H), 7.92 (d, 1H). GC-MS: m/z 471 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-1f88aaeb78b04d1dbb0434e39f2096a1
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…