Potassium Carbonate → HCID 67252653, compound

HRID 2427734Notes

Reaction equation

HRID 2427734 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.C[O:15][C:16](=O)[C:17]1[C:22]([I:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:18]=1[CH2:27]Br.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[N+:24]([C:20]1[CH:19]=[C:18]2[C:17](=[C:22]([I:23])[CH:21]=1)[C:16](=[O:15])[N:9]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([O:3][C:2]([F:12])([F:13])[F:1])=[CH:5][CH:6]=1)[CH2:27]2)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5718464-(Trifluoromethoxy)benzylamineHCID 67252692Methyl 2-(bromomethyl)-6-iodo-4-nitrobenzoate

Product 1

HCID 67252653HCID 67252653, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-trifluoromethoxy-benzyl amine (0.586 mL, 3.84 mmol), 2-bromomethyl-4-nitro-6-iodo-benzoic acid methyl ester (1.18 g, 2.95 mmol), and K2CO3 (0.815 g, 0.815 mmol) in toluene (7 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-nitro-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.144 g, 10%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.31 (s, 2H), 4.82 (s, 2H), 7.19 (d, 2H), 7.38 (d, 2H), 8.24 (s, 1H), 8.78 (s, 1H). GC-MS: m/z 478 (M)+, 409 (M−69)+.

Workup

  1. temperaturewas heated
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1a46edea6cd645daac9a613379f02ab7
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…