Ethyl Acetate → HCID 57949672, compound

HRID 2427619Notes

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:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][NH2:30])=[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:30]([CH2:29][CH2:28][CH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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 (0.106 g, 0.3 mmol), 3-(4-phenoxy-phenyl)-propylamine (0.136 g, 0.6 mmol), and K2CO3 (0.110 g, 0.8 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-(4-phenoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.025 g, 18%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.01 (m, 2H), 2.68 (t, 2H), 3.67 (t, 2H), 4.28 (s, 2H), 6.86-7.42 (m, 11H), 7.88 (d, 1H).

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-d292f4b675b04b34b25df25dd8631930
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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