Bromine → HCID 18624189, compound

HRID 1860655Notes

Reaction equation

HRID 1860655 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([CH3:20])([CH3:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:8][C:9]=1[OH:10]>C(Cl)(Cl)(Cl)Cl>[Br:1][C:8]1[CH:7]=[C:6]([CH2:11][C:12]([CH3:19])([CH3:20])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[C:4]([F:3])[C:9]=1[OH:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 18624166HCID 18624166, compound

Product 1

HCID 18624189HCID 18624189, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Bromine solution (12.4 ml, 12.4 mmol, 1.0 M in CCl4) was added a solution of the product of STEP 6 (1.58 g, 6.2 mmol) in 30 ml CCl4 at 0° C. over 5 min. The reaction was stirred at room temperature for 30 min, and quenched with saturated NaHCO3 solution. The product was extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed brine, dried with Na2SO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/ hexane=1/9) to give a colorless oil in 0.73 g. NMR spectra of the product were consistent for the proposed structure.

Workup

  1. customquenched with saturated NaHCO3 solution
  2. extractionThe product was extracted with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (on silica gel, ethyl acetate/ hexane=1/9)
  8. customto give a colorless oil in 0.73 g

Sources & evidence

ORD record
ord-9dfa5bd207cf42d9a5deb000014b6c10
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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