Trityl chloride → 6-Bromo-3-trityl-3H-benzooxazol-2-one

HRID 1280743Notes

Reaction equation

HRID 1280743 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[H-].[Na+].[C:14]1([C:20](Cl)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 298596-Bromo-2(3H)-benzoxazolone

Product 1

HCID 30970186-Bromo-3-trityl-3H-benzooxazol-2-oneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-Bromo-3H-benzooxazol-2-one (0.165 g, 0.77 mmol) was added portionwise into a 0° C. suspension of NaH (44.8 mg, 1mmol, 55%) in dry DMF (4 ml). After 1 hour stirring at room temperature, a solution of triphenylmethylchloride (0.24 g, 0.85 mmol) in DMF (0.5 ml) was added. The reaction mixture was stirred 1 hour at room temperature then quenched with H2O (15 ml). The aqueous phase was extracted with ethyl acetate, the combined organic phases were washed with H2O and brine, dried over Na2SO4 and concentrated to provide 6-bromo -3-trityl-3H-benzooxazol-2-one (0.27 g, 77 %) as a beige solid, MS: m/e=457.1 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred 1 hour at room temperature
  2. customthen quenched with H2O (15 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic phases were washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3457af16500b47e8a2c84421a997a9e8
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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