Methanol → 4-Chloro-2-iodobenzeneethanol

HRID 2189138Notes

Reaction equation

HRID 2189138 reaction equation
O1CCCC1.B.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](O)=[O:16])=[C:10]([I:18])[CH:9]=1.CO>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[C:10]([I:18])[CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 51357402HCID 51357402, compound

Product 1

HCID 686149434-Chloro-2-iodobenzeneethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 52.73 mmol of borane tetrahydrofuran complex (1N in tetrahydrofuran) is added dropwise to a stirred solution of 21.09 mmol of (4-chloro-2-iodo-phenyl)-acetic acid in 150 ml of dry tetrahydrofuran. The reaction mixture is stirred at room temperature for 1 hour then 20 ml of methanol are carefully added. The mixture is refluxed at 60° C. for 45 minutes, and then evaporated to dryness. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title product as a yellowish solid. Rf=0.13 (EtOAc-heptane=1:4); Rt=4.27 (gradient I).

Workup

  1. temperatureThe mixture is refluxed at 60° C. for 45 minutes
  2. customevaporated to dryness
  3. customThe resulting residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-1ec015bef29246bba13f6d044f50985c
Source dataset
uspto-grants-2012_12
Patent number
US08324235B2

Reaction notes

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