N-bromobutanimide → 6-(bromomethyl)-3,3-bis(fluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037028Notes

Reaction equation

HRID 1037028 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]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866854723,3-bis(fluoromethyl)-6-methylbenzo[c][1,2]oxaborol-1(3H)-ol

Product 1

HCID 866854746-(bromomethyl)-3,3-bis(fluoromethyl)benzo[c][1,2]oxaborol-1(3H)-olYield 87.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

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%).

Workup

  1. temperatureThe mixture was refluxed for 2 h under the light from a Sun lamp
  2. washwashed with aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-849be08935a84e45a728c884a97affc3
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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