Toluene → HCID 57967305, compound

HRID 535241Notes

Reaction equation

HRID 535241 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:20]=[CH:19][C:18]([C:21]4[O:22][C:23]5[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=5[N:25]=4)=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[Br:37]N1C(=O)CCC1=O>C(OCC)(=O)C>[Br:37][C:6]1[C:5]2[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=2)[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[O:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[N:25]=3)=[CH:19][CH:20]=2)=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[CH:11]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 67184N-bromobutanimideHCID 579673632-[4-(9-Anthryl)phenyl]benzoxazole

Product 1

HCID 57967305HCID 57967305, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 1 L Meyer flask, 3.3 g (8.8 mmol) of 2-[4-(9-anthryl)phenyl]benzoxazole, 50 mL of toluene, and 200 mL of ethyl acetate were placed. Into the solution, 1.6 g (8.8 mmol) of N-bromosuccinimide was added little by little. This solution was stirred under air for 25 hours. After a certain period, the solution was washed with water, a saturated aqueous solution of sodium hydrogen carbonate, and saturated saline, and then, the organic layer was dried with magnesium sulfate. The obtained mixture was gravity filtered, and the filtrate was condensed to give an oily substance. The oily substance was purified by silica gel column chromatography (toluene:hexane=5:1) to give a solid. The solid was recrystallized with toluene/methanol, giving 3.3 g of the target yellow powder in a yield of 82%.

Workup

  1. waitAfter a certain period
  2. washthe solution was washed with water
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and saturated saline, and then, the organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. customcondensed
  6. customto give an oily substance
  7. customThe oily substance was purified by silica gel column chromatography (toluene:hexane=5:1)
  8. customto give a solid
  9. customThe solid was recrystallized with toluene/methanol

Sources & evidence

ORD record
ord-da4f405962094ba0b7cf1e64dfde2caf
Source dataset
uspto-grants-2014_10
Patent number
US08859108B2

Reaction notes

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