4-Bromo-3,5-dimethoxybenzaldehyde → 1-(4-Bromo-3,5-dimethoxyphenyl)propan-1-ol

HRID 56584ノート

反応式

HRID 56584 の反応式
[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[CH2:14]([Mg]Br)[CH3:15]>C1COCC1>[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]([OH:7])[CH2:14][CH3:15])=[CH:4][C:3]=1[O:12][CH3:13]

参加物

4

反応物 2

HCID 30155794-Bromo-3,5-dimethoxybenzaldehydeHCID 178418443HCID 178418443、化合物

生成物 1

HCID 584320031-(4-Bromo-3,5-dimethoxyphenyl)propan-1-ol収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

An oven-dried flask under argon was charged with 4-bromo-3,5-dimethoxybenzaldehyde (5.0 g, 20.4 mmol) and anhydrous THF (30 mL). The mixture was cooled over ice then a solution of ethyl magnesium bromide (3.0 M in diethyl ether, 8.2 mL, 24.5 mmol) was added dropwise from an addition funnel over a period of 45 min. After stirring for 20 min, the mixture was allowed to warm to room temperature and stirred for 19 hrs. After quenching with a solution of aqueous NH4Cl, it was diluted with H2O and EtOAc then cooled over an ice bath. After the mixture was cooled, the layers were separated. The organics were washed with H2O and brine then dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in CH2Cl2 and concentrated in vacuo again to give 1-(4-bromo-3,5-dimethoxyphenyl)propan-1-ol as a clear oil (5.43 g, 97% yield). The product was used without further purification.

後処理

  1. temperatureThe mixture was cooled over ice
  2. stirringstirred for 19 hrs
  3. customAfter quenching with a solution of aqueous NH4Cl, it
  4. additionwas diluted with H2O and EtOAc
  5. temperaturethen cooled over an ice bath
  6. temperatureAfter the mixture was cooled
  7. customthe layers were separated
  8. washThe organics were washed with H2O and brine
  9. dry with materialthen dried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. dissolutionThe residue was dissolved in CH2Cl2
  12. concentrationconcentrated in vacuo again

出典と根拠

ORDレコード
ord-d78f5d49c04e4d8fa5c62fd429f3f3a4
出典データセット
uspto-grants-2016_09
特許番号
US09434707B2

反応ノート

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