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

HRID 535232Notes

Reaction equation

HRID 535232 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

In a 300 mL three-neck flask, 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 placed. This mixture was stirred for 4 hours under nitrogen stream. After a certain period, water was added to the mixture, and an aqueous layer was extracted with ethyl acetate. The resulting extracted solution and the organic layer were combined and washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and then the organic layer was dried with magnesium sulfate. The mixture obtained was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was condensed to give a solid. The solid was recrystallized with ethyl acetate/hexane, so that 3.1 g of target white powder was obtained in a yield of 61%.

Workup

  1. waitAfter a certain period
  2. extractionan aqueous layer was extracted with ethyl acetate
  3. extractionThe resulting extracted solution
  4. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline
  5. dry with materialthe organic layer was dried with magnesium sulfate
  6. customThe mixture obtained
  7. filtrationwas subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
  8. customcondensed
  9. customto give a solid
  10. customThe solid was recrystallized with ethyl acetate/hexane, so that 3.1 g of target white powder
  11. customwas obtained in a yield of 61%

Sources & evidence

ORD record
ord-b4cbaa6c29e840ce8529fcd25eaa0644
Source dataset
uspto-grants-2014_10
Patent number
US08859108B2

Reaction notes

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