Hydrochloric Acid → HCID 57825080, compound

HRID 1668715Notes

Reaction equation

HRID 1668715 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=1.[CH3:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=1)=O.Cl>O1CCCC1>[Br:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:18]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=2)=[CH2:17])[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 165023'-BromoacetophenoneHCID 2280881-Bromo-4-(propan-2-yloxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 57825080HCID 57825080, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (1.6 M solution in hexane, 12.0 mL, 0.9 eq) was added dropwise to a solution of 1-bromo-4-isopropoxy-benzene (4.8 g, 22 mmol, 1.0 eq) in tetrahydrofuran (20 mL) at −78° C. After stirring 30 min 3-bromoacetophenone (3.3 mL, 1.1 eq) in tetrahydrofuran (20 mL) was added dropwise. The mixture was allowed to warm up to room temperature and stirred for 2 h, then treated with 1 N HCl (10 mL), extracted with ethyl acetate, dried (sodium sulfate) and concentrated in vacuo. The crude material was dissolved in acetic acid (50 mL) and sulfuric acid (10 mL) and the mixture was warmed to 75° C. for 30 min, cooled at room temperature and 1 N NaOH was added up to pH=7. The aqueous phase was extracted with dichloromethane (3×10 mL), dried (sodium sulfate) the solvent was removed and the residue was purified by column chromatography (cyclohexane) to afford the title compound as a colourless oil (1.8 g, 25%);

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude material was dissolved in acetic acid (50 mL)
  6. temperaturesulfuric acid (10 mL) and the mixture was warmed to 75° C. for 30 min
  7. temperaturecooled at room temperature
  8. addition1 N NaOH was added up to pH=7
  9. extractionThe aqueous phase was extracted with dichloromethane (3×10 mL)
  10. dry with materialdried (sodium sulfate) the solvent
  11. customwas removed
  12. customthe residue was purified by column chromatography (cyclohexane)

Sources & evidence

ORD record
ord-867fbc2c276946c4a60e364f15182e6a
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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