Isopropyl iodide → 1-Bromo-2-[(propan-2-yl)oxy]benzene

HRID 612601Notes

Reaction equation

HRID 612601 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[CH:15](I)([CH3:17])[CH3:16]>C(O)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 72442-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 219254271-Bromo-2-[(propan-2-yl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Prepare a stirred mixture of ortho-bromo-phenol (25.951 g, 17.4 mL, 0.15 mole) and potassium carbonate (20.70 g, 0.16 mole) in 175 mL isopropanol at ambient temperature under argon. Slowly add isopropyl iodide (22.2 g, 16.00 mL), heat at reflux and stir the mixture overnight. Cool to ambient temperature then filter, condensing the filtrate on a rotary evaporator. Dissolve the residual oil in diethyl ether (300 mL) and twice extract with 100 mL 50% sodium hyroxide. Separate, wash with brine and concentrate on a rotary evaporator to give a pale yellow liquid. Distill on the Kugelrohr (0.05 mm, 100°-120° C.) to obtain the title compound as an oil. (24.21 g, 75%).

Workup

  1. customPrepare
  2. temperatureat reflux
  3. filtrationthen filter
  4. customcondensing the filtrate
  5. customon a rotary evaporator
  6. dissolutionDissolve the residual oil in diethyl ether (300 mL)
  7. extractiontwice extract with 100 mL 50% sodium hyroxide
  8. customSeparate
  9. washwash with brine
  10. concentrationconcentrate on a rotary evaporator
  11. customto give a pale yellow liquid
  12. distillationDistill on the Kugelrohr (0.05 mm, 100°-120° C.)

Sources & evidence

ORD record
ord-b757932acdd7444b92733299de2b5f67
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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