Water → 1-(Benzyloxy)-4-iodobenzene

HRID 1955453Notes

Reaction equation

HRID 1955453 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 696764-Iodoanisole

Product 1

HCID 5196711-(Benzyloxy)-4-iodobenzeneYield 88.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-iodoanisole (10.12 g, 0.046 mole), benzyl bromide (8.00 g, 0.046 mole), and potassium carbonate (6.31 g, 0.046 mole) in acetone (20 ml) were refluxed for 24 hours. Water was added and the aqueous layer extracted with ether (3×100 ml). The combined organic layers were washed with 2M NAOH (2×150 ml) and dried over anhydrous potassium carbonate. Evaporation of the solvent followed by crystallisation from methanol yielded 12.57 g (88%) benzyl 4-iodophenyl ether.

Workup

  1. extractionthe aqueous layer extracted with ether (3×100 ml)
  2. washThe combined organic layers were washed with 2M NAOH (2×150 ml)
  3. dry with materialdried over anhydrous potassium carbonate
  4. customEvaporation of the solvent
  5. customfollowed by crystallisation from methanol

Sources & evidence

ORD record
ord-3007ad268a1c4994b785278949c9a7c2
Source dataset
uspto-grants-1998_07
Patent number
US05776375

Reaction notes

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