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

HRID 1470922

Reaction equation

HRID 1470922 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, S and the solid product was collected by filtration 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. filtrationS and the solid product was collected by filtration
  3. washrinsed with benzene, water, methanol, and dichloromethane
  4. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-9f80fa95fee84f4f8a1b3dadd9dc502f
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Linked notes

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