4-Bromobenzaldehyde → 4-Bromo-alpha-ethylbenzenemethanol

HRID 1501055ノート

反応式

HRID 1501055 の反応式
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1>O1CCCC1>[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]([OH:11])[CH2:1][CH3:2])=[CH:8][CH:7]=1

参加物

4

反応物 2

HCID 707414-BromobenzaldehydeHCID 178418443HCID 178418443、化合物

生成物 1

HCID 1072904-Bromo-alpha-ethylbenzenemethanol収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Ethylmagnesium bromide (5.4 mL, 3 M solution in tetrahydrofuran) was added dropwise to the solution of 4-bromobenzaldehyde (2.0 g, 10.8 mmol) in tetrahydrofuran (30 mL) at −30° C. Then the resultant mixture stirred at room temperature for 4 hours. The reaction was quenched with saturated ammonium chloride aqueous. The organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give 1-(4-bromophenyl)propan-1-ol (2.0 g, 88%). 1H NMR (300 MHz, d6-DMSO): δ 7.49 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 5.20 (d, J=4.5 Hz, 1H), 4.45-4.41 (m, 1H), 1.63-1.53 (m, 2H), 0.80 (t, J=7.5 Hz, 3H).

後処理

  1. customThe reaction was quenched with saturated ammonium chloride aqueous
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue
  7. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-add373cdd3e84f7f96d4b427fe968e5d
出典データセット
uspto-grants-2015_12
特許番号
US09206128B2

反応ノート

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