Benzyl Bromide → 1-(3-Iodophenyl)-2-phenylethan-1-one

HRID 876634Notes

Reaction equation

HRID 876634 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[I:1][C:2]1[CH:3]=[C:4]([C:5](=[O:7])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 120603-Iodobenzoic acid

Product 1

HCID 247238831-(3-Iodophenyl)-2-phenylethan-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

m-Iodobenzoic acid (1 g, 0.004 mol) was dissolved in MeCN (20 ml), Cs2CO3 (2.63 g, 2 eq) and benzyl bromide (0.528 ml, 1.1 eq) added. The mixture was heated at reflux overnight. The mixture was concentrated, taken up in EtOAc, washed with water, dried (MgSO4), and concentrated. The residue was purified by silica gel chromatography (0-60% EtOAc in hexane) to give 1.6 g of M16-3.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-60% EtOAc in hexane)
  8. customto give 1.6 g of M16-3

Sources & evidence

ORD record
ord-3b97f9e4898f48fba9591abb81abf3d5
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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