Hydrochloric Acid → HCID 86724264, compound

HRID 594868Notes

Reaction equation

HRID 594868 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2([CH:18]=[CH2:19])[CH2:13][C:12](OC)([O:14]C)[CH2:11]2)=[C:4]([I:20])[CH:3]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2([CH:18]=[CH2:19])[CH2:13][C:12](=[O:14])[CH2:11]2)=[C:4]([I:20])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86724265HCID 86724265, compound

Product 1

HCID 86724264HCID 86724264, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 4-bromo-1-[(3,3-dimethoxy-1-vinylcyclobutyl)methoxy]-2-iodobenzene (3.16 g, 6.98 mmol) and 1M aqueous HCl (14 mL) in THF (31 mL) was stirred for ambient temperature for 1 hour. Then the mixture was stirred for 4 hours at 50° C. The mixture was cooled to room temperature and added saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure to give 3-[(4-bromo-2-iodophenoxy)methyl]-3-vinylcyclobutanone (2.91 g).

Workup

  1. stirringThen the mixture was stirred for 4 hours at 50° C
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8e8d38054ca048d4a4d292090ff43da8
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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