Isopropanol → HCID 4102537, compound

HRID 1805891Notes

Reaction equation

HRID 1805891 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][C:5]2=[O:12].[C:13]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:18]=CC=C[CH:14]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C(O)(C)C>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH:13]([CH3:18])[CH3:14])[C:5]2=[O:12]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 2360184-Bromophthalimide

Product 1

HCID 4102537HCID 4102537, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-bromo-1H-isoindole-1,3(2H)-dione (ABCR, 5.0 g) and triphenylphosphine (8.70 g) in tetrahydrofuran (THF) (100 mL) under nitrogen at room temperature was added di-t-butyl azodicarboxylate (7.64 g). The suspension was cooled in an ice/water bath and to this was added iso-propanol (2.032 mL). The reaction mixture was allowed to warm to room temperature to give a pale yellow solution. After 60 minutes, the solvent was removed in vacuo and the residue was dissolved in DCM (30 mL). This was applied to a 750 g silica cartridge and eluted with a gradient of 0-40% ethyl acetate in cyclohexane over 8CV. The required fractions were combined and evaporated in vacuo to give the title compound (5.27 g) as a pale yellow solid.

Workup

  1. temperatureThe suspension was cooled in an ice/water bath
  2. customto give a pale yellow solution
  3. customthe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in DCM (30 mL)
  5. washeluted with a gradient of 0-40% ethyl acetate in cyclohexane over 8CV
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-fb5cc92bb23b4baf833f0f06c7dff1d9
Source dataset
uspto-grants-2013_01
Patent number
US08354539B2

Reaction notes

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