Ethyl Acetate → 2-[3-(3-Bromophenyl)-propyl]-2,3-dihydroisoindol-1-one

HRID 2427557Notes

Reaction equation

HRID 2427557 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][NH2:11])[CH:5]=[CH:6][CH:7]=1.C[O:13][C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21]Br.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:21][C:16]3[C:15](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]2=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 183675463-(3-Bromophenyl)propan-1-amine

Product 1

HCID 579498072-[3-(3-Bromophenyl)-propyl]-2,3-dihydroisoindol-1-oneYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(3-bromophenyl)-propylamine (7.86 g, 36.7 mmol), 2-bromomethyl-benzoic acid methyl ester (8.45 g, 36.7 mmol), and K2CO3 (6.91 g, 50 mmol) in toluene (100 mL) was heated at reflux with stirring for 1.5 h. Workup and silica gel column chromatography using a gradient of hexanes to 50% ethyl acetate in hexanes afforded 2-[3-(3-bromophenyl)-propyl]-2,3-dihydroisoindol-1-one (8.81 g, 73%). GC/MS gave: m/z (rel.int.) 331 (M+, 10), 329 (M+, 10), 147-(100), 146 (72) 119 (25), and 91 (38). 1H NMR (300 MHz, CDCl3): δ 2.00 (dt, 2H), 2.67 (t, 2H), 3.67 (t, 2H), 4.36 (s, 2H), 7.14 (dd, 2H), 7.31 (m, 1H), 7.35 (br s, 1H), 7.45 (m, 2H), 7.51 (dt, 1H), 7.85 (d, 1H). 13C NMR (300 MHz, CDCl3): δ 29.9, 32.8, 42.0, 49.9, 122.4, 122.7, 123.6, 127.1, 128.0, 129.1, 130.0, 131.2, 131.3 132.8, 141.1, 143.7, 168.6.

Workup

  1. temperaturewas heated
  2. temperatureat reflux

Sources & evidence

ORD record
ord-fd85e45984fb44a7bf9fa405c00dac00
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…