Ethyl Acetate → 7-Iodo-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427618Notes

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.200 g, 0.56 mmol), 4-phenoxy-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 7-iodo-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.108 g, 44%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.19 (s, 2H), 4.75 (s, 2H), 6.94-7.40 (m, 1H), 7.92 (d, 1H). GC-MS: m/z 441 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-4e9aaec0beab4d45bef1839e96f81c64
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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