Ethyl Acetate → HCID 57949414, compound

HRID 2427655Notes

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]([F:28])([F:27])[O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([NH2:26])[CH3:25])=[CH:20][CH:19]=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:26]([CH:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][C:16]([F:15])([F:27])[F:28])=[CH:23][CH:22]=1)[CH3:25])[CH2:12]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-2-bromomethyl-6-chloro-benzoic acid methyl ester (0.409 g, 1.2 mmol), 1-(4-trifluoromethoxy-phenyl)-ethyl-amine (0.288 g, 10.4 mmol), and K2CO3 (0.331 g, 2.4 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-[1-(4-trifluoromethoxy-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (0.202 g, 39%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.67 (d, 3H), 3.96 (d, 1H), 4.20 (d, 1H), 5.77 (q, 1H) 7.21 (d, 2H), 7.41 (m, 3H), 7.58 (s, 1H). GC-MS: m/z 434 (M)+, 420 (M−14)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-b3990697f9b24193862c2ce57d367fc9
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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