Ethyl Acetate → HCID 57672259, compound

HRID 252075Notes

Reaction equation

HRID 252075 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[CH2:8]2.C[O-].[Na+].CO.[C:33](OCC)(=[O:35])C>CO.CCCCCC>[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([O:35][CH3:33])[CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[CH2:8]2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23694274Sodium methanolate methanolHCID 866299795-Bromo-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one

Product 1

HCID 57672259HCID 57672259, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-trifluoromethyl-5-bromo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.060 g, 0.15 mmol), and 30% sodium methoxide-methanol (0.21 mL) in methanol (4 mL) was stirred at 100° C. for 1 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-trifluoromethyl-5-methoxy-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.043 g, 70%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.88 (s, 3H), 4.25 (s, 2H), 4.76 (s, 2H), 7.02 (s, 1H), 7.17 (d, 2H), 7.28 (s, 1H), 7.37 (d, 2H).

Sources & evidence

ORD record
ord-77a4e642a8c74c2f953895d088f9727a
Source dataset
uspto-grants-2011_01
Patent number
US07868008B2

Reaction notes

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