Sodium Hydroxide → 2,6-Dichloro-3-methylphenol

HRID 1875131노트

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HRID 1875131 반응식
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[C:3]=1[CH3:11].[OH-].[Na+]>[Zn]>[Cl:10][C:4]1[C:3]([CH3:11])=[CH:2][CH:7]=[C:6]([Cl:8])[C:5]=1[OH:9]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 156210804-Bromo-2,6-dichloro-3-methylphenol

생성물 1

HCID 835212,6-Dichloro-3-methylphenol수율 88%

시약·촉매·용매 1

HCID 23994Zinc촉매

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온도
100 °C

실험 절차

Zn powder (9.84 g, 150 mmol) was added to a solution of 4-bromo-2,6-dichloro-3-methylphenol (4.92 g, 19.22 mmol) in 10% NaOH (50 ml, 125 mmol). The reaction mixture was stirred for 1 h at 100° C. and then cooled down to RT. The Zn powder was filtered off and the filtrate was acidified with 10% HCl and extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluted with 0-5% EtOAc in hexane to give the title compound as a colorless oil (2.98 g, 88%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.14 (1H, d) 6.76 (1H, d) 5.83 (1H, s) 2.34 (3H, s). LCMS: m/z 175 (M−1).

후처리

  1. temperaturecooled down to RT
  2. filtrationThe Zn powder was filtered off
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluted with 0-5% EtOAc in hexane

출처 및 근거

ORD 기록
ord-e4668ad99e074991832bfbb4ec7712c8
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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