Boron tribromide → Benzoxazole

HRID 1368037Notes

Reaction equation

HRID 1368037 reaction equation
CO[C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](C3C=CC=C(C(F)(F)F)C=3)=[N:8][C:7]=2[CH:21]=1.B(Br)(Br)Br>C(Cl)Cl>[O:10]1[C:6]2[CH:5]=[CH:4][CH:3]=[CH:21][C:7]=2[N:8]=[CH:9]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 121354125-Methoxy-2-(3-trifluoromethylphenyl)-benzoxazole

Product 1

HCID 9228Benzoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 10 (200 mg, 0.68 mmol) in CH2Cl2 (5 mL) was added BBr3 (1M in CH2Cl2, 1 mL, 1 mmol) dropwise. The resulting solution was allowed to stir for 48 h. The solvent was removed by evaporation (in vacuo) and the residue was dissolved in ethyl acetate and washed with saturated NaHCO3. The organic layer was dried over MgSO4 and evaporated (in vacuo). The residue was purified using column chromatography (30% ethyl acetate/hexanes) to yield compound 8 as a white solid.

Workup

  1. customThe solvent was removed by evaporation (in vacuo)
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated (in vacuo)
  6. customThe residue was purified

Sources & evidence

ORD record
ord-eea5a4b85e7748f9bf6cb9bfc397def2
Source dataset
uspto-grants-2003_06
Patent number
US06573264B1

Reaction notes

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