tert-Butanol → 1,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-dione

HRID 2364781

Reaction equation

HRID 2364781 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]([Cl:34])=[C:30]([N+:35]([O-:37])=[O:36])[CH:29]=1)=[O:27]>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH2:19][CH2:25][C:26]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([N+:35]([O-:37])=[O:36])[CH:29]=2)=[O:27])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8021DiethylamineHCID 795964'-Chloro-3'-nitroacetophenoneHCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-one

Product 1

HCID 866490991,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-dione

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

Zinc chloride (27.4 g, 201 mmol), diethylamine (15.6 mL, 151 mmol) and t-butanol (14.4 mL, 151 mmol) were combined in benzene (151 mL) at room temperature under a nitrogen atmosphere and stirred for 2 h. 1-(4-chloro-3-nitrophenyl)ethanone (30.1 g, 151 mmol) and 2-bromo-1-(4-chloro-3-nitrophenyl)ethanone (28 g, 101 mmol) were added. The mixture was stirred vigorously for 20 h, and the solid product was collected by filteration and rinsed with benzene, water, methanol, and dichloromethane. The solid was dried in a vacuum oven.

Workup

  1. stirringThe mixture was stirred vigorously for 20 h
  2. customthe solid product was collected by filteration
  3. washrinsed with benzene, water, methanol, and dichloromethane
  4. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-108a162284974588bcea8ba907eebf9d
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Linked notes

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