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

HRID 1097166Notes

Reaction equation

HRID 1097166 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=O)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[O:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 8310534-bromo-N-(2-hydroxyphenyl)benzamide

Product 1

HCID 128467152-(4-Bromophenyl)benzo(d)oxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.3 g (18 mmol) of 4-bromo-N-(2-hydroxyphenyl)benzamide, 8.0 g (46 mmol) of para-toluenesulfonic acid monohydrate, and 200 mL of toluene were put in a 300 mL three-neck flask. The mixture was refluxed for 4 hours under a nitrogen stream. After a certain time, water was added to the mixture, and an organic layer and an aqueous layer was extracted with ethyl acetate. The resulting extract was combined with the organic layer, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and then a saturated saline, and dried with magnesium sulfate. The obtained mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was condensed to obtain a solid. The obtained solid was recrystallized with ethyl acetate/hexane, so that 3.1 g of target white powder was obtained with a yield of 61%.

Workup

  1. temperatureThe mixture was refluxed for 4 hours under a nitrogen stream
  2. extractionan organic layer and an aqueous layer was extracted with ethyl acetate
  3. extractionThe resulting extract
  4. washthe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materiala saturated saline, and dried with magnesium sulfate
  6. filtrationThe obtained mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
  7. customcondensed
  8. customto obtain a solid
  9. customThe obtained solid was recrystallized with ethyl acetate/hexane, so that 3.1 g of target white powder
  10. customwas obtained with a yield of 61%

Sources & evidence

ORD record
ord-1f8145ae17ea49d88b36b2ea444274d1
Source dataset
uspto-grants-2012_03
Patent number
US08142911B2

Reaction notes

Loading…