Methyl 3-iodobenzoate → HCID 13216677, compound

HRID 2057999Notes

Reaction equation

HRID 2057999 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:12][C:13]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:14]=1[Cu]>C1(C)C=CC=CC=1>[F:12][C:13]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:14]=1[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[CH2:5][OH:7].[F:12][C:13]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:14]=1[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 69258Methyl 3-iodobenzoateHCID 178505970HCID 178505970, compound

Product 2

HCID 13216677HCID 13216677, compoundYield 191.2%HCID 15588650HCID 15588650, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(2,3,4,5,6-Pentafluorophenyl)benzyl alcohol was prepared as follows: Under an argon atmosphere, methyl 3-iodobenzoate (2.3 g. 0.009 mole) and 2,3,4,5,6-pentafluorophenyl copper (2.0 g, 0.009 mole) were added to 50 ml of toluene. The stirred reaction mixture was heated under reflux for 2 hours, then cooled to room temperature. The mixture was filtered and the filtrate evaporated under reduced pressure to a residual solid. The solid was recrystallized from methanol to give methyl 3-(2,3,4,5,6-pentafluorophenyl)benzoate (2.6 g); mp, 104°-106°.

Workup

  1. customThe stirred reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 2 hours
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated under reduced pressure to a residual solid
  6. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-6711f27b926840d89b9a93419d9a2ff3
Source dataset
uspto-grants-1980_07
Patent number
US04214004

Reaction notes

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