Potassium Carbonate → 5-Fluoro-7-iodo-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427732Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.C[O:14][C:15](=O)[C:16]1[C:21]([I:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=1[CH2:24]Br.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:23][C:19]1[CH:18]=[C:17]2[C:16](=[C:21]([I:22])[CH:20]=1)[C:15](=[O:14])[N:8]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:11])([F:12])[F:1])=[CH:4][CH:5]=1)[CH2:24]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-trifluoromethyl-benzyl amine (0.142 mL, 1.0 mmol), 2-bromomethyl-4-fluoro-6-iodo-benzoic acid methyl ester (0.270 g, 0.73 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (4 mL) was heated with stirring at 100° C. for 2 h. The resulting mixture was filtered and concentrated. Silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-fluoro-7-iodo-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.110 g, 35%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.18 (s, 2H), 4.84 (s, 2H), 7.10 (d, 1H), 7.42 (d, 2H), 7.60 (m, 2H), 7.66 (d, 1H). GC-MS: m/z 435 (M)+, 416 (M−19)+.

Workup

temperaturewas heated
filtrationThe resulting mixture was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-0086b224c04a47f7b95e8397b4d8c9e8
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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