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

HRID 76135Notes

Reaction equation

HRID 76135 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

Conditions

Temperature
80 °C

Procedure

3.44 mL (45.8 mmol) 1-propanol is added to an ice cold mixture of 3.42 g (30.5 mmol) KOtBu in 18 mL DMF. After stirring the mixture for 10 min 1.80 g (7.63 mmol) 4-fluoro-1-iodo-2-methylbenzene are added and the reaction mixture is stirred at 80° C. for 3 h. The reaction is quenched by the addition of a sat. aq. NH4Cl solution and extracted with EtOAc (2×). The combined organic layers are washed with sat. aq. NH4Cl solution and brine, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, heptane/EtOAc 9/1).

Workup

  1. additionare added
  2. customThe reaction is quenched by the addition of a 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 with Na2SO4
  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-1fd5b82ef14e4689a84cf2f39b300bc9
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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