N-bromobutanimide → HCID 86685469, compound

HRID 1037102Notes

Reaction equation

HRID 1037102 reaction equation
[CH2:1]([C:3]1([CH2:14][CH3:15])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:4]1=2)[CH3:2].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]([CH2:1][CH3:2])([CH2:14][CH3:15])[O:7][B:6]([OH:8])[C:5]=2[CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86685467HCID 86685467, compound

Product 1

HCID 86685469HCID 86685469, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3,3-diethyl-6-methylbenzo[c][1,2]oxaborol-1(3H)-ol (0.8 g, 3.92 mmol) in CCl4 (10 mL) under nitrogen was added NBS (698 mg, 3.92 mmol) and BPO (94 mg, 0.39 mmol). The mixture was refluxed for 2 h under the light from 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 (0.8 g, 72%).

Workup

  1. temperatureThe mixture was refluxed for 2 h under the light from 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-9568581b5e484a5585cb14146f94527c
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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