1,3-Dibromopropane → HCID 20061256, compound

HRID 1085304Notes

Reaction equation

HRID 1085304 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].[Br:25][CH2:26][CH2:27][CH2:28]Br>CC(CC)=O>[Br:25][CH2:26][CH2:27][CH2:28][O:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 2311504-Hydroxy-3-nitrobenzophenone

Product 1

HCID 20061256HCID 20061256, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-hydroxy-3-nitrobenzophenone (2.5 g) and 7.1 g of potassium carbonate were suspended in 15 ml methylethylketone. The suspension was stirred under heating with reflux for 30 minutes, added with 1,3-dibromopropane and then heated with reflux for 6 hours. The reaction mixture was cooled down to room temperature, and insoluble substances were removed by filtration. The filtrate was then concentrated, and the resultant precipitate was subjected to silica gel column chromatograph (hexane/ethyl acetate=3.1 (v/v)) for purification; thereby 2.08 g of an oil, 4-(3-bromopropyloxy)-3-nitrobenzophenone, was obtained.

Workup

  1. temperatureunder heating
  2. temperaturewith reflux for 30 minutes
  3. temperatureheated
  4. temperaturewith reflux for 6 hours
  5. custominsoluble substances were removed by filtration
  6. concentrationThe filtrate was then concentrated
  7. customthe resultant precipitate was subjected to silica gel column chromatograph (hexane/ethyl acetate=3.1 (v/v)) for purification

Sources & evidence

ORD record
ord-91d45b1af358408aa49d05fdd84a0eaa
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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