Ethyl Acetate → HCID 57949424, compound

HRID 2427596Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-benzoic acid methyl ester (0.460 g, 2.0 mmol), 3-(4-trifluoromethoxy-phenyl)-propylamine (0.438 g, 2.0 mmol), and K2CO3 (0.500 g, 3.6 mmol) in toluene (10 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-(4-trifluoromethoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.248 g, 37%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.97 (m, 2H), 2.70 (t, 2H), 3.69 (t, 2H), 4.36 (s, 2H), 7.09 (d, 2H), 7.23 (t, 2H), 7.42-7.56 (m, 3H), 7.86 (d, 1H). GC-MS: m/z 335 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-45ffc39561144979bc07fc48a5ae1fb7
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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