Hydrochloric Acid → Phenol, 2,4-difluoro-5-methyl-

HRID 1771734Notes

Reaction equation

HRID 1771734 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 84648928Phenol, 2,4-difluoro-5-methyl-Yield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-138bce7bdd554fa291859150200f44d9
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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