Hexane → 5-Chloro-2-(1-oxo-1,3-dihydroisoindol-2-ylmethyl)benzonitrile

HRID 2427575Notes

Reaction equation

HRID 2427575 reaction equation
C1(=O)C2C(=CC=CC=2)C[NH:2]1.Br[CH2:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].C([O-])([O-])=O.[Cs+].[Cs+].C1[O:45][CH2:44][CH2:43]OCCOCCOCCOCCOC1.[CH3:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]>CC(C)=O.C(OCC)(=O)C>[Cl:21][C:19]1[CH:18]=[CH:17][C:14]([CH2:15][N:16]2[CH2:51][C:50]3[C:43](=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:44]2=[O:45])=[C:13]([CH:20]=1)[C:12]#[N:2]

Participants

8

Reactant 5

HCID 8058HexaneHCID 10199PhthalimidineHCID 10796Cesium carbonateHCID 2855718-Crown-6HCID 126680532-(Bromomethyl)-4-chlorobenzonitrile

Product 1

HCID 672524625-Chloro-2-(1-oxo-1,3-dihydroisoindol-2-ylmethyl)benzonitrileYield 41%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,3-dihydro-isoindol-1-one (0.066 g, 0.5 mmol), 2-bromomethyl-4-chloro-benzonitrile (0.116 g, 0.6 mmol), Cs2CO3 (0.408 g, 1.25 mmol), and 18-crown-6 (0.013 g, 0.05 mmol) in acetone (3 mL) was stirred at 70° C. for 16 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-chloro-2-(1-oxo-1,3-dihydroisoindol-2-ylmethyl)benzonitrile (0.057 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.48 (s, 2H), 5.08 (s, 2H), 7.42-7.65 (m, 611), 7.92 (d, 1H). GC-MS: m/z 282 (M)+.

Sources & evidence

ORD record
ord-ce6e8af3aff34718b83727afe57a22c1
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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