Ethyl Acetate → HCID 67252143, compound

HRID 2427671Notes

Reaction equation

HRID 2427671 reaction equation
CO[C:3](=[O:14])[C:4]1[C:9]([I:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[CH2:12]Br.[F:15][C:16]([F:27])([F:26])[O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Cl:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([I:10])[CH:8]=1)[C:3](=[O:14])[N:23]([CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][C:16]([F:15])([F:26])[F:27])=[CH:19][CH:20]=1)[CH2:12]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5718464-(Trifluoromethoxy)benzylamineHCID 67251492HCID 67251492, compound

Product 1

HCID 67252143HCID 67252143, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-bromomethyl-6-iodo-benzoic acid methyl ester (0.78 g, 2.0 mmol), 4-trifluoromethoxy-benzylamine (0.458 mL, 3.0 mmol), and K2CO3 (0.552 g, 4.0 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography of the product using 30% ethyl acetate in hexane afforded 5-chloro-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.356 g, 38%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.17 (s, 2H), 4.78 (s, 2H) 7.20 (d, 2H), 7.37 (t, 3H), 7.93 (s, 1H). GC-MS: m/z 467 (M)+, 382 (M−85)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-5fc63eba75434d488357b4fa52c77a9f
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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