Benzyl Bromide → 1-(Benzyloxy)-4-iodo-2-methylbenzene

HRID 1442679Notes

Reaction equation

HRID 1442679 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]=1[CH3:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 1437134-Iodo-2-methylphenol

Product 1

HCID 589043791-(Benzyloxy)-4-iodo-2-methylbenzeneYield 90.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mechanically stirred mixture of 4-iodo-2-methylphenol (1.62 moles; 391 g), cesium carbonate (1.99 moles; 650 g), and 1.75 L of acetone is treated with benzyl bromide (1.70 moles; 203 mL; 291 g) over 15 m. The reaction mixture was stirred for 21 h at RT and filtered. The filter cake is washed with 1 L of acetone, and the combined filtrates are concentrated. The crude semi-solid is recrystallized from pentane to give 475 grams (90%) of the desired product as a white solid. 1H NMR (CDCl3) δ: 7.40 (m, 7H), 6.64 (d, J=8.6 Hz, 1H), 5.06 (s, 2H), 2.24 (s, 3H).

Workup

  1. filtrationfiltered
  2. washThe filter cake is washed with 1 L of acetone
  3. concentrationthe combined filtrates are concentrated
  4. customThe crude semi-solid is recrystallized from pentane

Sources & evidence

ORD record
ord-bf8fef0443054050b62f00400810c522
Source dataset
uspto-grants-2010_02
Patent number
US07659296B2

Reaction notes

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