Toluene → 7-Bromo-2-tert-butyl-6-(3-hydroxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17279Notes

Reaction equation

HRID 17279 reaction equation
C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:20][C:21]1[C:26]([OH:27])=[C:25]([NH:28][C:29](=O)[C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([C:35]#[N:36])=[C:23]([CH3:37])[C:22]=1[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=1>O>[Br:20][C:21]1[C:22]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=2)=[C:23]([CH3:37])[C:24]([C:35]#[N:36])=[C:25]2[C:26]=1[O:27][C:29]([C:30]([CH3:32])([CH3:31])[CH3:33])=[N:28]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86630804N-(2-Bromo-5-cyano-3,3'-dihydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

Product 1

HCID 685850047-Bromo-2-tert-butyl-6-(3-hydroxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Toluene (45 ml), p-toluenesulfonic acid monohydrate (21.0 mg, 111 μmol) were added to N-(2-bromo-5-cyano-3,3′-dihydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide (I-16) (446 mg, 1.11 mmol), followed by refluxing with a Dean-Stark condenser for 3 hours. After cooling, water (50 ml) was added to the reaction liquid, the product was extracted with ethyl acetate (50 ml×2). The organic layer was washed with saturated brine (50 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the entitled compound (404 mg, 95%) as a colorless solid.

Workup

  1. temperatureby refluxing with a Dean-Stark condenser for 3 hours
  2. temperatureAfter cooling
  3. extractionthe product was extracted with ethyl acetate (50 ml×2)
  4. washThe organic layer was washed with saturated brine (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0bbb1f0ef9f34865b1c08f15cf05cf63
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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