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Diethyl Ether → 2-[2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-benzyl]-isoindole-1,3-dione

HRID 1181050
Notes
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Reaction equation

HRID 1181050 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[CH:4][C:3]=1[CH2:16]Br.CN(C=O)C.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K].CCOCC>O>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[CH:4][C:3]=1[CH2:16][N:27]1[C:23](=[O:33])[C:24]2[C:25](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:26]1=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 19437125(4-Bromo-3-bromomethyl-phenoxy)-tert-butyl-dimethyl-silaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 179843932-[2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-benzyl]-isoindole-1,3-dioneYield 68.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
18 °C

Procedure

A 12 L flask was charged with (4-bromo-3-bromomethyl-phenoxy)-tert-butyl-dimethyl-silane (568 g 1.49 mol), DMF (3.1 L), and potassium phthalimide (316 g 1.71 mol). An exotherm to 34° C. occurred. After 40 min, the reaction mixture was cooled to 18° C. Ether (6.2 L) and DI water (4.9 L) were added, and the layers were separated. The organic layer was washed with saturated NaCl solution (2 L), dried (Na2SO4), filtered, and concentrated. The residue was recrystallized from heptane (1.5 L) to give the title compound (454 g, 68%).

Workup

  1. customto 34° C.
  2. customthe layers were separated
  3. washThe organic layer was washed with saturated NaCl solution (2 L)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from heptane (1.5 L)

Sources & evidence

ORD record
ord-b6849d905b1b4cb69f8ebab7cb5ef3d8
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07282501B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes