Boron tribromide → Benzoxazole
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe solvent was removed by evaporation (in vacuo)
- dissolutionthe residue was dissolved in ethyl acetate
- washwashed with saturated NaHCO3
- dry with materialThe organic layer was dried over MgSO4
- customevaporated (in vacuo)
- customThe residue was purified
Sources & evidence
- ORD record
- ord-8ac68bc3d6084837bdd5e28d1f8cad1a
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06849632B2
Reaction notes
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