Ethyl Acetate → HCID 57949287, compound

HRID 2427650Notes

Reaction equation

HRID 2427650 reaction equation
CO[C:3](=[O:14])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[CH2:12]Br.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Br:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([Cl:10])[CH:8]=1)[C:3](=[O:14])[N:21]([CH2:20][C:19]1[CH:22]=[CH:23][C:16]([F:15])=[CH:17][CH:18]=1)[CH2:12]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 673264-FluorobenzylamineHCID 59512234Methyl 4-bromo-2-(bromomethyl)-6-chlorobenzoate

Product 1

HCID 57949287HCID 57949287, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-bromomethyl-6-chloro-benzoic acid methyl ester (1.06 g, 3.00 mmol), 4-fluoro-benzylamine (0.457 mL, 4.0 mmol), and K2CO3 (0.967 g, 7.0 mmol) in toluene (10 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-bromo-7-chloro-2-(4-fluoro-benzyl)-2,3-dihydro-isoindol-1-one (0.21 g, 20%). GC-MS: m/z 355 (M)+. 1H NMR (300 MHz, CDCl3): δ (ppm) 4.20 (s, 2H), 4.73 (s, 2H), 7.02 (t, 2H), 7.29-7.31 (m, 2H), 7.44 (s, 1H), 7.58 (s, 1H).

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-71e8a28cbd9b4c9e83f75d19788999e2
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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