1-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene → 2-But-1-ynyl-5-fluoro-phenol

HRID 423180

Reaction equation

HRID 423180 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[O:12]COC)#[C:2][CH2:3][CH3:4]>Cl.CC(C)=O.CCOCC>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[OH:12])#[C:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 595651761-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene

Product 1

HCID 595651802-But-1-ynyl-5-fluoro-phenolYield 73.9%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

1-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene (6.1 g, 29 mmol) is dissolved in 250 mL of a 10% solution of concentrated HCl in acetone. The solution is stirred at room temperature for 5 h. The reaction is diluted with ether and washed with saturated aqueous NaHCO3 and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage® Si65M, 5% AcOEt/hexane) to yield 3.52 g (73%) of the title compound as an orange oil. GCMS m/e 164[M]+.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic portion is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by flash chromatography (Biotage® Si65M, 5% AcOEt/hexane)

Sources & evidence

ORD record
ord-9f4eded38863413c8b61709ddb5a6b2b
Source dataset
uspto-grants-2012_01
Patent number
US08101761B2

Linked notes

Loading…