Ethyl Acetate → HCID 57949761, compound

HRID 2427651Notes

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.[CH2:15]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1)[CH3:16].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:22]([CH2:21][C:20]1[CH:23]=[CH:24][C:17]([CH2:15][CH3:16])=[CH:18][CH:19]=1)[CH2:12]2

Participants

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-ethyl-benzylamine (0.575 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-ethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.442 g, 41%). GC-MS: m/z 364 (M)+, 336 (M−28)+. 1H NMR (300 MHz, CDCl3): δ (ppm) 1.24 (t, 3H), 2.64 (q, 2H) 4.20 (s, 2H), 4.73 (s, 2H), 7.21 (m, 4H), 7.44 (s, 1H), 7.58 (s, 1H).

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-1180a021a4b24e539a4aaaf2ed369bac
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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