Benzyl Bromide → 0-Benzyl-3,5-dimethyl-4-iodophenol

HRID 1638425Notes

Reaction equation

HRID 1638425 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([CH3:9])[C:7]=1[I:8].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([C:5]1[C:6]([CH3:9])=[C:7]([I:8])[C:2]([CH3:1])=[CH:3][C:4]=1[OH:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27362644-Iodo-3,5-dimethyl-phenol

Product 1

HCID 198425240-Benzyl-3,5-dimethyl-4-iodophenolYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0-Benzyl-3,5-dimethyl-4-iodophenol was prepared as follows: In a 500 ml round-bottom flask were placed 30.0 g (121 mmol) of 3,5-dimethyl-4-iodophenol, 190 ml acetone, 16.9 g (122 mmol) potassium carbonate and 20.7 g (121 mmol) benzyl bromide. The mixture was refluxed for 15 hours, cooled, filtered and the precipitate washed with acetone. The combined filtrate was evaporated under reduced pressure to yield an orange oil which slowly crystallized. This was dissolved in methylene chloride and water and the methylene chloride layer sequentially washed with 5% sodium hydroxide, saturated sodium bisulfite and water. After drying over magnesium sulfate and filtering, the methylene chloride was removed under reduced pressure. The resulting solid was recrystallized from hot methanol, cooled to room temperature and then in ice, collected and washed with cold methanol to yield 27.9 g (68% yield) of white plates, mp 56-57, which were identified as O-Benzy13,5-dimethyl-4-iodophenol. 1H NMR analysis indicated: (δ, CDCl3) 7.68 (m, 5H), 6.62 (s, 2H), 4.88 (s, 2H) and 2.39 (s, 6H). Mass spectrum analysis indicated: (m/e) 338 (M+) and 91.

Workup

  1. customIn a 500 ml round-bottom flask were placed
  2. temperatureThe mixture was refluxed for 15 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe precipitate washed with acetone
  6. customThe combined filtrate was evaporated under reduced pressure
  7. customto yield an orange oil which
  8. customslowly crystallized
  9. dissolutionThis was dissolved in methylene chloride
  10. washwater and the methylene chloride layer sequentially washed with 5% sodium hydroxide, saturated sodium bisulfite and water
  11. dry with materialAfter drying over magnesium sulfate
  12. filtrationfiltering
  13. customthe methylene chloride was removed under reduced pressure
  14. customThe resulting solid was recrystallized from hot methanol
  15. customin ice, collected
  16. washwashed with cold methanol
  17. customto yield 27.9 g (68% yield) of white plates, mp 56-57, which

Sources & evidence

ORD record
ord-852bf050042e4b16bb49075f52349016
Source dataset
uspto-grants-1989_11
Patent number
US04879398

Reaction notes

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