Potassium Carbonate → Bromo-7-methoxy-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one

HRID 2427542Notes

Reaction equation

HRID 2427542 reaction equation
CO[C:3](=[O:14])[C:4]1[C:9](C)=[CH:8][C:7](Br)=[CH:6][C:5]=1[CH2:12][Br:13].[F:15][C:16]([F:27])([F:26])[O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.[C:28]([O-])([O-])=[O:29].[K+].[K+]>C1(C)C=CC=CC=1>[Br:13][CH:12]1[C:5]2[C:4](=[C:9]([O:29][CH3:28])[CH:8]=[CH:7][CH:6]=2)[C:3](=[O:14])[N:23]1[CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][C:16]([F:26])([F:27])[F:15])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5718464-(Trifluoromethoxy)benzylamineHCID 59512232HCID 59512232, compound

Product 1

HCID 67250179Bromo-7-methoxy-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-oneYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Bromo-2-bromomethyl-6-methylbenzoic acid methyl ester (762 mg, 2.37 mmol), 4-trifluoromethoxy benzylamine (0.543 mL, 3.56 mmol) and K2CO3 (981 mg, 7.10 mmol) were stirred in toluene (10 mL) at 95° C. for 12 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (10-25% EtOAc/Hexanes) to afford a yellow oil (650 mg, 66%). 1H NMR (300 MHz, CDCl3): δ 7.33-7.36 (m, 2H), 7.18 (d, 2H), 7.13 (s, 1H), 7.07 (s, 1H), 4.75 (s, 2H), 4.22 (s, 2H), 4.00 (s, 3H).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by column chromatography (10-25% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-c8891f0104c14584ad0b668e5f99363b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…