Ammonium Chloride → 1-(4-Bromo-2-chlorophenyl)ethanol

HRID 1501272노트

반응식

HRID 1501272 반응식
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[C:7]([Cl:13])[CH:6]=1.[Cl-].[NH4+]>O1CCCC1>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:12])[CH3:1])=[C:7]([Cl:13])[CH:6]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 43805739(4-Bromo-2-chlorophenyl)methanolHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 202581281-(4-Bromo-2-chlorophenyl)ethanol수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

A solution of methylmagnesium bromide (4.8 mL, 3M, 14.4 mmol) was added dropwise to the solution of (4-bromo-2-chlorophenyl)methanol (1.52 g, 7.0 mmol) in tetrahydrofuran at −40° C. Then the mixture was stirred at 25° C. for 3 hrs. Saturated ammonium chloride solution (10 mL) was added to the mixture. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give 1-(4-bromo-2-chlorophenyl)ethanol as a white solid (1.32 g, 81%). 1H NMR (300 MHz, d6-DMSO): 7.69 (d, J=8.1, 1H), δ 7.53 (d, J=0.9, 1H), 7.19 (dd, J1=8.1, 1H J2=0.9, 1H), 5.38 (d, J=3.6, 1H), δ 4.70 (m, 1H), 1.30 (d, J=6.6, 3H).

후처리

  1. concentrationThe mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-45f890bf7ada403e9d29ce8ad92af26c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

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