Cyclohexyl bromide → N-cyclohexyloxyphthalimide

HRID 600958Notes

Reaction equation

HRID 600958 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].C1OCCOCCOCCOCCOCCOC1.[CH:37]1(Br)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>CS(C)=O.O>[CH:37]1([O:7][N:8]2[C:9](=[O:18])[C:10]3[C:11](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:13])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

7

Reactant 4

HCID 7960Cyclohexyl bromideHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 2855718-Crown-6

Product 1

HCID 10467039N-cyclohexyloxyphthalimideYield 93%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Solid potassium carbonate (6.91 g, 50.0 mmol) was added to a solution of N-hydroxyphthalimide (4.08 g, 25.0 mmol) and 18-crown-6 (661 mg, 2.5 mmol) in dimethyl sulfoxide (62 mL), and the mixture was stirred at 25° C. for 5 min. To the mixture cyclohexyl bromide (12.3 mL, 100.0 mmol) was added, and the mixture stirred at 80° C. for 3 h. After ice-cooling, the mixture was poured into cold water and the resulting precipitate was collected by filtration in vacuo, washed with water (25 mL) and hexanes (15 mL) and dried in vacuo to afford 2-cyclohexyloxy-isoindole-1,3-dione (5.67 g, 93%) as a white solid which was used in the next step without further purification.

Workup

  1. stirringthe mixture stirred at 80° C. for 3 h
  2. temperatureAfter ice-cooling
  3. filtrationthe resulting precipitate was collected by filtration in vacuo
  4. washwashed with water (25 mL) and hexanes (15 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-46185667d80246249f0f6c1bdd70dcd2
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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