Hydrochloric Acid → 4-[3-Chloro-4-(1-methyl-2-oxo-ethyl)-phenoxy]-benzonitrile

HRID 1095900

Reaction equation

HRID 1095900 reaction equation
CC(C)([O-])C.[K+].[C:7]([C:10]1[CH:24]=[CH:23][C:13]([O:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)=[CH:12][C:11]=1[Cl:25])(=O)[CH3:8].[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.[C:50]([O-:53])(O)=O.[Na+]>C1COCC1>[Cl:25][C:11]1[CH:12]=[C:13]([CH:23]=[CH:24][C:10]=1[CH:7]([CH3:8])[CH:50]=[O:53])[O:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 643355014-(4-Acetyl-3-chlorophenoxy)benzonitrile

Product 1

HCID 866459484-[3-Chloro-4-(1-methyl-2-oxo-ethyl)-phenoxy]-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (248 mg) was added to a solution 4-(4-acetyl-3-chloro-phenoxy)-benzonitrile (500 mg) and (methoxymethyl)-triphenylphosphonium chloride (694 mg) in THF (10 ml) at room temperature. The mixture was stirred for 1 h at room temperature. 25% aqueous HCl (4 ml) was added. The resulting mixture was stirred 1 h at room temperature and poured then carefully to a saturated aqueous NaHCO3 solution. After neutralization, the mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (450 mg) as yellow oil. MS (m/e, ISP neg. ion)=284.3 [M−H+].

Workup

  1. stirringThe resulting mixture was stirred 1 h at room temperature
  2. additionpoured
  3. extractionAfter neutralization, the mixture was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2)

Sources & evidence

ORD record
ord-e8ddd91e87ed4d8bb16d6688a903ae58
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Linked notes

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