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

HRID 1641983Notes

Reaction equation

HRID 1641983 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-necked flask were placed 5.3 g (18 mmol) of 4-bromo-N-(2-hydroxyphenyl)benzamide, 8.0 g (46 mmol) of p-toluenesulphonic acid monohydrate, and 200 mL of toluene. This mixture was refluxed for 4 hours under nitrogen stream. After a predetermined time, water was added to the mixture that had been refluxed, and an aqueous layer and an organic layer were separated in the mixture. Then, an organic substance was extracted from the aqueous layer with ethyl acetate. The extract and the organic layer were neutralized together with a saturated aqueous sodium hydrogen carbonate solution, and washed with a saturated aqueous sodium chloride solution. Then, the organic layer was dried over magnesium sulfate. This mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was concentrated 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. customIn a 300 mL three-necked flask were placed
  2. temperatureThis mixture was refluxed for 4 hours under nitrogen stream
  3. temperaturehad been refluxed
  4. customan aqueous layer and an organic layer were separated in the mixture
  5. extractionThen, an organic substance was extracted from the aqueous layer with ethyl acetate
  6. extractionThe extract
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialThen, the organic layer was dried over magnesium sulfate
  9. filtrationThis mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
  10. concentrationthe filtrate was concentrated
  11. customto obtain a solid
  12. customThe obtained solid was recrystallized with ethyl acetate/hexane, so that 3.1 g of target white powder
  13. customwas obtained with a yield of 61%

Sources & evidence

ORD record
ord-777c80d2968f4dfd905c1d6ee048b3b1
Source dataset
uspto-grants-2012_02
Patent number
US08119259B2

Reaction notes

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