Hydrochloric Acid → HCID 21996967, compound

HRID 1976324Notes

Reaction equation

HRID 1976324 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:8].N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25].Cl>ClCCl>[C:24]([O:17][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:16][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:8])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 21996975HCID 21996975, compound2×

Product 1

HCID 21996967HCID 21996967, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a yellow solution of 229 mg (0.8 mmol) of 5-bromo-2-hydroxy-4′-methylbenzophenone (Compound K) in 15 mL of dichloromethane (under a blanket of argon) was added 0.07 mL (69 mg, 0.9 mmol) of pyridine followed by 0.07 mL (74 mg, 0.9 mmol) of acetyl chloride. The resultant reaction mixture was stirred at ambient temperature overnight (16.75 hours), poured into 10% HCl (aq.) solution and extracted with ethyl acetate. The layers were separated and the aqueous phase was washed with ethyl acetate. The organic phases were combined and then sequentially washed with sat. NaHCO3 (aq.) solution, water and brine, dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. Purification by flash chromatography (silica, 20% ethyl acetate in hexane) gave the title compound as a clear, colorless oil.

Workup

  1. customThe resultant reaction mixture
  2. extractionextracted with ethyl acetate
  3. customThe layers were separated
  4. washthe aqueous phase was washed with ethyl acetate
  5. washsequentially washed with sat. NaHCO3 (aq.) solution, water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a yellow oil
  10. customPurification by flash chromatography (silica, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2029c56b1987440dbb78a9f5098ac2d2
Source dataset
uspto-grants-2001_05
Patent number
US06225494B1

Reaction notes

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