Ethyl Acetate → HCID 11544193, compound

HRID 2427584Notes

Reaction equation

HRID 2427584 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[O:13]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[O:13]([C:20]1[CH:21]=[CH:22][C:23]([CH2:24][N:25]2[CH2:10][C:5]3[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:3]2=[O:12])=[CH:26][CH:27]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 2760343(4-Phenoxyphenyl)methanamine

Product 1

HCID 11544193HCID 11544193, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-benzoic acid methyl ester (0.115 g, 0.5 mmol), 4-phenoxy-benzylamine (0.106 mL, 0.6 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (3 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-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.095 g, 61%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.28 (s, 2H), 4.79 (s, 2H), 6.98-7.54 (m, 12H), 7.89 (d, 1H). GC-MS: m/z 315 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-c15edf9964e84af98f19b73422f7250c
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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