Ethyl Acetate → 2-(3-Phenoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427585Notes

Reaction equation

CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[O:13]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH2:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[O:13]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][N:24]1[CH2:10][C:5]2[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:3]1=[O:12])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-benzoic acid methyl ester (0.115 g, 0.5 mmol), 3-phenoxy-benzylamine (0.106 mL, 0.6 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (3 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(3-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.064 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.26 (s, 2H), 4.82 (s, 2H), 6.90-7.56 (m, 12H), 7.89 (d, 1H). GC-MS: m/z 315 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-e8e3b56c26354a49a749f6fd6a2f9f71
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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