Triethylamine → 2-(2-Bromomethyl-benzyloxy)-isoindole-1,3-dione

HRID 1582292

Reaction equation

HRID 1582292 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].CCN(CC)CC.[Br:20][CH2:21][C:22]1[C:23]([CH2:28]Br)=[CH:24][CH:25]=[CH:26][CH:27]=1>CN(C=O)C>[Br:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 66665o-Bis(bromomethyl)benzene

Product 1

HCID 219851622-(2-Bromomethyl-benzyloxy)-isoindole-1,3-dioneYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-hydroxyphthalimide (0.60 g, 3.68 mmol) and Et3N (0.60 mL, 4.30 mmol) in DMF (6 mL) was added α,α′-dibromo-o-xylene (3.30 g, 0.0125 mol) and the mixture stirred at room temperature for 4 h. The resultant brown precipitate was filtered and washed with CH2Cl2. The filtrate was diluted with EtOAc (40 mL) and water (30 mL) and the organic phase washed with brine (1×30 mL), dried (Na2SO4) and concentrated under reduced pressure. The resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc) to give the title compound (581 mg, 46%) as a white solid. 1H NMR (CDCl3) δ4.99 (s, 2H), 5.37 (s, 2H), 7.27-7.40 (m, 2H), 7.41-7.45 (m, 2H), 7.73-7.76 (m, 2H), 7.81-7.84 (m, 2H).

Workup

  1. filtrationThe resultant brown precipitate was filtered
  2. washwashed with CH2Cl2
  3. additionThe filtrate was diluted with EtOAc (40 mL) and water (30 mL)
  4. washthe organic phase washed with brine (1×30 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc)

Sources & evidence

ORD record
ord-e1ba1fd89c434498a655f168340c1bc8
Source dataset
uspto-grants-2004_05
Patent number
US06734191B2

Linked notes

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