Benzylamine → 2-Benzyl-5-bromo-2,3-dihydro-1H-isoindol-1-one

HRID 2427635Notes

Reaction equation

HRID 2427635 reaction equation
CO[C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1[CH2:11]Br.[CH2:14]([NH2:21])[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>[CH2:14]([N:21]1[CH2:11][C:5]2[C:4](=[CH:9][CH:8]=[C:7]([Br:10])[CH:6]=2)[C:3]1=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 231582302-Benzyl-5-bromo-2,3-dihydro-1H-isoindol-1-oneYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-bromomethyl-benzoic acid methyl ester (0.308 g, 1.0 mmol), benzylamine (0.218 mL, 2.0 mmol), and K2CO3 (0.553 g, 4.0 mmol) in toluene (6 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-benzyl-5-bromo-2,3-dihydro-isoindol-1-one (0.150 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.22 (s, 2H), 4.76 (s, 2H), 7.21-7.38 (m, 5H), 7.52 (s, 1H), 7.61 (d, 1H), 7.76 (d, 1H). GC-MS: m/z 302 (M)+, 226 (M−76)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-e58a08b8caaa47f0b697a1fd1e65570b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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