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Ethyl Acetate → 5-Bromo-7-chloro-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427648
Notes
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Reaction equation

HRID 2427648 reaction equation
CO[C:3](=[O:14])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[CH2:12]Br.[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Br:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([Cl:10])[CH:8]=1)[C:3](=[O:14])[N:21]([CH2:20][C:19]1[CH:22]=[CH:23][C:16]([Cl:15])=[CH:17][CH:18]=1)[CH2:12]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 660364-ChlorobenzylamineHCID 59512234Methyl 4-bromo-2-(bromomethyl)-6-chlorobenzoate

Product 1

HCID 116393035-Bromo-7-chloro-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-oneYield 41%

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-bromomethyl-6-chloro-benzoic acid methyl ester (0.900 g, 2.65 mmol), 4-chloro-benzylamine (0.391 mL, 3.2 mmol), and K2CO3 (0.69 g, 5.0 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 5-bromo-7-chloro-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one (0.391 g, 41%). GC-MS: m/z 371 (M)+, 336 (M−35)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-4bd5453561f54b5a96fa161034995f01
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968570B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes