Hydrochloric Acid → HCID 82780306, compound

HRID 2096792Notes

Reaction equation

HRID 2096792 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[Cl:17])=O.Cl.[C:19]([O-:22])(O)=O.[Na+]>C1COCC1>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:8]([CH3:7])[CH:19]=[O:22])=[C:11]([Cl:17])[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 155609501-(4-Bromo-2-chlorophenyl)ethan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 82780306HCID 82780306, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (7.53 g) was added to a solution 2-chloro-4-bromoacetophenone (CAS Reg. No. 252561-81-2, 10.45 g) and (methoxymethyl)-triphenylphosphosium chloride (21.48 g) in THF (100 ml) at room temperature. The mixture was stirred for 1 h at room temperature. 25% aqueous HCl (90 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 1:4) to give the title compound (8.1 g) as a yellow oil. MS (m/e, ISP neg. ion)=247.2 [M−H+].

Workup

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

Sources & evidence

ORD record
ord-a058e267bba245418fd1769c0996749e
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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