Ethyl Acetate → HCID 11661991, compound

HRID 2427630Notes

Reaction equation

HRID 2427630 reaction equation
CO[C:3](=[O:13])[C:4]1[C:9]([I:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.[F:14][C:15]([F:26])([F:25])[O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[I:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:13])[N:22]([CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][C:15]([F:14])([F:25])[F:26])=[CH:18][CH:19]=1)[CH2:11]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5718464-(Trifluoromethoxy)benzylamineHCID 11268261Methyl 2-(bromomethyl)-6-iodobenzoate

Product 1

HCID 11661991HCID 11661991, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.245 g, 0.7 mmol), 4-trifluoromethoxy-benzylamine (0.122 mL, 0.8 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.095 g, 31%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.21 (s, 2H), 4.82 (s, 2H), 6.84 (d, 2H), 7.14-7.40 (m, 4H), 7.92 (d, 1H). GC-MS: m/z 433 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-fc83b5c42d324621a0d72337db733479
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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