Acetone → HCID 59133385, compound

HRID 1715872Notes

Reaction equation

HRID 1715872 reaction equation
[C:1]([C:20]1[CH:26]=[CH:25][C:23](N)=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.N([O-])=O.[Na+].[BrH:35]>O.[Cu]Br>[C:1]([C:20]1[CH:26]=[CH:25][C:23]([Br:35])=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 260Hydrogen Bromide2×HCID 89914Benzenamine, 4-(triphenylmethyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 59133385HCID 59133385, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 962WaterSolvent

Procedure

25 parts by weight of 4-tritylaniline, 400 parts by weight of acetone, and 162 parts by weight of hydrobromic acid were put into a reaction vessel and stirred. While cooling the vessel in an ice bath, a solution of 7 parts by weight of sodium nitrite dissolved in 100 parts by weight of water was slowly added dropwise thereto. After the dropwise addition was complete, stirring was carried out for 30 minutes in an ice bath. Slowly added dropwise to this solution in an ice bath was a solution of 17.4 parts by weight of copper (I) bromide that had been dissolved in 31.5 parts by weight of hydrobromic acid. After the dropwise addition was complete, stirring was carried out at room temperature for 2 hours. After the reaction, a precipitate deposited in the reaction solution was collected by filtration, thus giving 25.8 parts by weight of 4-tritylbromobenzene (yield: 86%).

Workup

  1. temperatureWhile cooling the vessel in an ice bath
  2. additionwas slowly added dropwise
  3. additionAfter the dropwise addition
  4. stirringstirring
  5. additionSlowly added dropwise to this solution in an ice bath
  6. additionAfter the dropwise addition
  7. stirringstirring
  8. waitwas carried out at room temperature for 2 hours
  9. customAfter the reaction
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-0eb6b09969544f54a5d8b3fc683348d1
Source dataset
uspto-grants-2010_09
Patent number
US07799949B2

Reaction notes

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