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

HRID 76135ノート

反応式

HRID 76135 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1fd5b82ef14e4689a84cf2f39b300bc9
出典データセット
uspto-grants-2014_09
特許番号
US08835472B2

反応ノート

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