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

HRID 1771734노트

반응식

HRID 1771734 반응식
[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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 79020345HCID 79020345, 화합물

생성물 1

HCID 846489282,4-Difluoro-5-methylphenol수율 66.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-138bce7bdd554fa291859150200f44d9
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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