N-bromobutanimide → 6-(bromomethyl)-3,3-bis(fluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol
Reaction equation
[F:1][CH2:2][C:3]1([CH2:14][F:15])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:4]1=2.C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:13][C:10]1[CH:11]=[CH:12][C:4]2[C:3]([CH2:14][F:15])([CH2:2][F:1])[O:7][B:6]([OH:8])[C:5]=2[CH:9]=1Participants
4
Procedure
To a solution of 3,3-bis(fluoromethyl)-6-methylbenzo[c][1,2]oxaborol-1(3H)-ol (0.5 g, 2.36 mmol) in CCl4 (10 mL) under nitrogen was added NBS (420 mg, 2.36 mmol) and BPO (57 mg, 0.236 mmol). The mixture was refluxed for 2 h under the light from a Sun lamp, and then it was cooled to rt, washed with aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to provide the product (0.6 g, yield 87.4%).