Hydrochloric Acid → 2,4-Difluoro-5-methylphenol

HRID 1771734ノート

反応式

HRID 1771734 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.[OH-:19].[Na+].OO.Cl>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1[OH:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 79020345HCID 79020345、化合物

生成物 1

HCID 846489282,4-Difluoro-5-methylphenol収率 66.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(2,4-difluoro-5-methyl-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.24 g, 8.82 mmol, 1.0 eq) in a mixture of NaOH (1M aqueous solution, 26.4 mL, 26.4 mmol, 3.0 eq) and THF (20 mL) at 0° C. was added H2O2 (3 g, 26.4 mmol, 3 eq). The reaction mixture was stirred at room temperature for 4 h, then the pH of the reaction mixture was adjusted to pH 5 by addition of 1M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude residue obtained was purified by column chromatography (petroleum ether: EtOAc, 100:1 to 50:1) to give the title compound as a colorless oil (850 mg, 65%).

後処理

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe combined organic extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude residue obtained
  7. customwas purified by column chromatography (petroleum ether: EtOAc, 100:1 to 50:1)

出典と根拠

ORDレコード
ord-138bce7bdd554fa291859150200f44d9
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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