Water → 1-(Benzyloxy)-2-iodobenzene

HRID 1859634Notes

Reaction equation

HRID 1859634 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CC(C)=O.CCCCCCC.CCOC(C)=O>[CH2:15]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[I:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 107842-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 119842101-(Benzyloxy)-2-iodobenzeneYield 82.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

In a 25 mL ovendried flask 2-iodophenol (1.03 g, 4.7 mmol) and potassium carbonate (0.71 g, 5.2 mmol) were dissolved in dry acetone (10 mL). The mixture was stirred for 15 min followed by addition of benzylbromide (0.61 mL, 5.2 mmol) and left over-night at rt. Addition of H2O (50 mL) followed by extraction with ethyl acetate (3×50 mL) and the combined organic phases were dried (MgSO4) and evaporated to dryness, to produce 1.7 g of crude 25. The crude product was subjected to CC [eluent: Heptane:EtOAc (9:1)] to give pure 25 (1.2 g, 81%). LC-MS [M+H]+ 310 (cald. 310.0).

Workup

  1. waitleft over-night at rt
  2. extractionfollowed by extraction with ethyl acetate (3×50 mL)
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. customevaporated to dryness
  5. customto produce 1.7 g of crude 25

Sources & evidence

ORD record
ord-91f2c34bb44b40159c5278dffaaa5534
Source dataset
uspto-grants-2003_03
Patent number
US06528529B1

Reaction notes

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