Cesium carbonate → HCID 57949531, compound

HRID 2427559Notes

Reaction equation

HRID 2427559 reaction equation
Br[CH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[C:17]1(=[O:26])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[N:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.C(OCC)(=O)C>[C:7]([C:6]1[CH:15]=[CH:16][C:3]([CH2:2][N:18]2[CH2:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:17]2=[O:26])=[CH:4][CH:5]=1)(=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2855718-Crown-6HCID 1229514-(Bromomethyl)benzophenoneHCID 1911091-Oxoisoindole

Product 1

HCID 57949531HCID 57949531, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(bromomethyl)benzophenone (138 mg, 0.5 mmol), isoindolone (67 mg, 0.5 mmol), cesium carbonate (407 mg, 1.25 mmol), and 18-crown-6 (13 mg, 0.05 mmol) in acetone (10 mL) was stirred heating at reflux for 3 h. Workup and silica gel column chromatography using a gradient of hexanes to 50% ethyl acetate in hexanes afforded 2-(4-benzoylbenzyl)-2,3-dihydroisoindol-1-one (149 mg, 91%). GC/MS gave: m/z (rel.int.) 327 (M+, 97), 250 (5), 222 (42), 196 (20) 165 (31), 146 (31), 133 (53), 119 (94), 105 (71), 91 (100), and 77 (98). 1H NMR (300 MHz, CDCl3): δ 4.33 (s, 2H), 4.89 (s, 2H), 7.42 (d, 2H), 7.45-7.59 (m, 6H), 7.77 (dd, 4H), 7.91 (dd, 1H).

Workup

  1. temperatureheating
  2. temperatureat reflux for 3 h

Sources & evidence

ORD record
ord-7ad9a624ec0a455ea6be5d147149330d
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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