Boron tribromide → Benzoxazole

HRID 22700

Reaction equation

HRID 22700 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-8ac68bc3d6084837bdd5e28d1f8cad1a
Source dataset
uspto-grants-2005_02
Patent number
US06849632B2

Linked notes

Loading…