2-Iodobenzylic alcohol → 2-(4-Chlorophenyl)benzyl alcohol

HRID 1750740Notes

Reaction equation

HRID 1750740 reaction equation
I[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](C2C=CC=CC=2B(O)O)=[CH:13][CH:12]=1>C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 1076292-Iodobenzylic alcoholHCID 234509984'-Chlorobiphenyl-2-boronic acid

Product 1

HCID 13927802-(4-Chlorophenyl)benzyl alcohol

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-iodobenzyl alcohol (11.0 g), 4-chlorophenylbenzeneboronic acid (8.5 g), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (800 mg) in Na2CO3 (2M solution, 94 mL) and dioxane (300 mL) was heated to 80° C. for 24 hours. The mixture was cooled, the layers were separated, and the organic layer was condensed. The resulting residue was purified by silica gel chromatography eluting with 20% ethyl acetate in hexanes to give the desired product.

Workup

  1. temperatureThe mixture was cooled
  2. customthe layers were separated
  3. customcondensed
  4. customThe resulting residue was purified by silica gel chromatography
  5. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7ee65dd410d74e2ab8bb4295062cb0ae
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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