Sulfuric Acid → HCID 67236410, compound

HRID 2364867Notes

Reaction equation

HRID 2364867 reaction equation
C(NCC)C.C(O)(C)(C)C.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22].Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=1)=[O:27].S(=O)(=O)(O)O>[Cl-].[Zn+2].[Cl-].C1C=CC=CC=1>[Br:34][C:31]1[CH:32]=[CH:33][C:28]([C:26](=[O:27])[CH2:25][CH2:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([Cl:11])=[C:13]([N+:21]([O-:23])=[O:22])[CH:14]=2)=[O:20])=[CH:29][CH:30]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 74544-Bromophenacyl bromideHCID 8021DiethylamineHCID 795964'-Chloro-3'-nitroacetophenone

Product 1

HCID 67236410HCID 67236410, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

Zinc chloride (2.73 g, 20 mmole)was treated with anhydrous benzene (10 mL) followed by diethylamine (1.55 mL, 15 mmole) and tert-butanol (1.4 mL, 15 mmole) and the resulting slurry was stirred at room temperature for 1.75 hr until all solids had dissolved. To the cloudy suspension was added 4′-chloro-3′-nitroacetophenone followed by 2,4′-dibromoacetophenone and the resulting light yellow slurry was stirred at room temperature for 68 hours. The resulting thick white slurry was treated with 25 mL 5% aqueous sulfuric acid with stirring and the resulting slurry was filtered. The solid was washed with water (50 mL), MeOH (50 mL) and CH2Cl2 (50 mL), then dried in vacuo at room temperature for 1 hr and at 55° C. for 5 hr. giving the title compound as a white solid, 3.4 g, 86%.

Workup

  1. dissolutionhad dissolved
  2. stirringthe resulting light yellow slurry was stirred at room temperature for 68 hours
  3. stirringwith stirring
  4. filtrationthe resulting slurry was filtered
  5. washThe solid was washed with water (50 mL), MeOH (50 mL) and CH2Cl2 (50 mL)
  6. customdried in vacuo at room temperature for 1 hr and at 55° C. for 5 hr

Sources & evidence

ORD record
ord-9ca051cbe1fe4f7e9b24c5db8586b343
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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