2-Aminophenol → 2-(4-Bromophenyl)benzo(d)oxazole

HRID 2354526Notes

Reaction equation

HRID 2354526 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]2[O:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 6101p-Toluenesulfonic acidHCID 707414-Bromobenzaldehyde

Product 1

HCID 128467152-(4-Bromophenyl)benzo(d)oxazoleYield 65.12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-aminophenol 7.86 g (72 mmole), 4-bromobenzaldehyde 16 g (87 mmole), and 2.8 g of PTSA (14 mmole) was stirred in 150 ml of Toluene, the reaction mixture was then heated to reflux for 16 hours, after cooling, the reaction mixture was extracted with water, and then the organic layer was evaporated to dry, the residue was then recrystallized with acetone to get 12.85 g of product (yield=65.12%).

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureto reflux for 16 hours
  3. temperatureafter cooling
  4. extractionthe reaction mixture was extracted with water
  5. customthe organic layer was evaporated
  6. customto dry
  7. customthe residue was then recrystallized with acetone

Sources & evidence

ORD record
ord-1f8a236d597c464eb2842600bf2758d7
Source dataset
uspto-grants-2010_07
Patent number
US07754348B2

Reaction notes

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