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

HRID 1875131ノート

反応式

HRID 1875131 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 835212,6-Dichloro-3-methylphenol収率 88%

試薬・触媒・溶媒 1

HCID 23994Zinc触媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e4668ad99e074991832bfbb4ec7712c8
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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