Ethyl Acetate → 5-Bromo-7-methyl-2-(4-phenoxybenzyl)-2,3-dihydroisoindol-1-one

HRID 2427691Notes

Reaction equation

CO[C:3](=[O:14])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[CH2:12]Br.[O:15]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Br:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([CH3:10])[CH:8]=1)[C:3](=[O:14])[N:27]([CH2:26][C:25]1[CH:28]=[CH:29][C:22]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:23][CH:24]=1)[CH2:12]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-2-bromomethyl-6-methyl-benzoic acid methyl ester (0.500 g, 1.6 mmol), 4-phenoxy-benzylamine (0.342 mL, 1.92 mmol), and K2CO3 (0.484 g, 3.5 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 5-bromo-7-methyl-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.212 g, 32%). GC-MS: m/z 407 (M)+, 314 (M−93)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-2e7c39b8868442a6bfad9243faf36345
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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