Ethyl Acetate → HCID 11717332, compound

HRID 2427679Notes

Reaction equation

CO[C:3](=[O:17])[C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:7]([Cl:14])=[CH:6][C:5]=1[CH2:15]Br.[CH2:18]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1)[CH3:19].C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Cl:14][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([C:10]([F:11])([F:12])[F:13])[CH:8]=1)[C:3](=[O:17])[N:25]([CH2:24][C:23]1[CH:26]=[CH:27][C:20]([CH2:18][CH3:19])=[CH:21][CH:22]=1)[CH2:15]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-2-bromomethyl-6-trifluoromethyl-benzoic acid methyl ester (0.995 g, 3.0 mmol), 4-ethyl-benzylamine (0.520 mL, 3.6 mmol), and K2CO3 (0.621 g, 4.5 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-chloro-2-(4-ethyl-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.30 g, 28%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.24 (t, 3H), 2.63 (q, 2H), 4.27 (s, 2H), 4.76 (s, 2H) 7.20 (m, 4H), 7.59 (s, 1H), 7.78 (s, 1H). GC-MS: m/z 353 (M)+, 338 (M−15)+, 324 (M−29)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-ec5d59bbc9a64bb3aad5b391ed9edf9e
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

Loading…