1-Propanol → 1-Iodo-2-methyl-4-propoxybenzene

HRID 330832Notes

Reaction equation

HRID 330832 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].CC([O-])(C)C.[K+].F[C:12]1[CH:17]=[CH:16][C:15]([I:18])=[C:14]([CH3:19])[CH:13]=1>CN(C=O)C>[I:18][C:15]1[CH:16]=[CH:17][C:12]([O:4][CH2:1][CH2:2][CH3:3])=[CH:13][C:14]=1[CH3:19]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 27745254-Fluoro-1-iodo-2-methylbenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 666142871-Iodo-2-methyl-4-propoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.44 mL (45.8 mmol) 1-propanol are added to 3.42 g (30.5 mmol) KOtBu in 18 mL DMF at 0° C. After stirring the solution for 10 min at rt, 1.80 g (7.63 mmol) 4-fluoro-1-iodo-2-methylbenzene are added and the mixture is stirred at 80° C. for 3 h. The reaction is quenched by the addition of sat. aq. NH4Cl solution and extracted with EtOAc (2×). The combined organic layers are washed with sat. aq. NH4Cl solution and brine, dried over sodium sulphate and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, heptane/EtOAc 9/1).

Workup

  1. stirringthe mixture is stirred at 80° C. for 3 h
  2. customThe reaction is quenched by the addition of sat. aq. NH4Cl solution
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers are washed with sat. aq. NH4Cl solution and brine
  5. dry with materialdried over sodium sulphate
  6. customthe solvent is removed in vacuo
  7. customThe crude product is purified by column chromatography (silica gel, heptane/EtOAc 9/1)

Sources & evidence

ORD record
ord-b9b7a802b1d44ac4891ce2f16df3c00d
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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