Benzyl Bromide → 1-(Benzyloxy)-2-iodobenzene

HRID 1723888Notes

Reaction equation

HRID 1723888 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.CCCCCCC.CCOC(C)=O>CC(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

6

Reactant 4

HCID 7498Benzyl BromideHCID 107842-IodophenolHCID 11430Potassium CarbonateHCID 21899848Ethylacetate heptane

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 25 mI 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 H20 (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. additionAddition of H20 (50 mL)
  3. extractionfollowed by extraction with ethyl acetate (3×50 mL)
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. customevaporated to dryness
  6. customto produce 1.7 g of crude 25

Sources & evidence

ORD record
ord-d7220a45a22342f2b1699a733ef55bad
Source dataset
uspto-grants-2009_02
Patent number
US07485651B2

Reaction notes

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