4-Bromobenzaldehyde → 4-Bromo-alpha-ethylbenzenemethanol

HRID 1501055노트

반응식

HRID 1501055 반응식
[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

참가 물질

4

반응물 2

HCID 707414-BromobenzaldehydeHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 1072904-Bromo-alpha-ethylbenzenemethanol수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-add373cdd3e84f7f96d4b427fe968e5d
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

반응 노트

불러오는 중…