Hydrogen Peroxide → N-(4-bromo-2-fluorophenyl)-5,7-dimethylbenzo[d]oxazol-2-amine

HRID 1397476

Reaction equation

HRID 1397476 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[F:11][C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[N:19]=[C:20]=S.O[Li].O.OO>O1CCCC1>[Br:18][C:16]1[CH:15]=[CH:14][C:13]([NH:19][C:20]2[O:10][C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[N:1]=2)=[C:12]([F:11])[CH:17]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1005306-Amino-2,4-xylenolHCID 168937Lithium hydroxide, monohydrateHCID 27570034-Bromo-2-fluorophenylisothiocyanate

Product 1

HCID 22347267N-(4-bromo-2-fluorophenyl)-5,7-dimethylbenzo[d]oxazol-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An ambient solution of 2-amino-4,6-dimethylphenol (0.85 g, 6.2 mmol) and 2-fluoro-4-bromophenyl isothiocyanate (1.44 g, 6.20 mmol) in tetrahydrofuran (20 mL) was stirred for 16 h. The reaction was cooled (0° C.), and LiOH.H2O (0.521 g, 12.41 mmol) was added, followed by the dropwise addition of 30% H2O2 (3.41 mL, 31.0 mmol) over 15 minutes. The reaction was warmed to room temperature and stirred for 16 h. The reaction was then quenched by the addition of 20% aqueous sodium sulfite; solution (50 mL) and ethyl acetate (75 mL). The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×75 mL). The combined organics were dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 gel, eluting with 25% ethyl acetate in hexane, to give the title compound. MS (ESI) m/z 335 [M+H]+.

Workup

  1. additionwas added
  2. customThe reaction was then quenched by the addition of 20% aqueous sodium sulfite
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with additional ethyl acetate (2×75 mL)
  5. dry with materialThe combined organics were dried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on SiO2 gel
  9. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3aeac27d846d4e9c99049251a98b0cc6
Source dataset
uspto-grants-2014_12
Patent number
US08901152B2

Linked notes

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