N-bromobutanimide → 6-(bromomethyl)-1H-spiro[benzo[c][1,2]oxaborole-3,1'-cyclopentan]-1-ol

HRID 1037034Notes

Reaction equation

HRID 1037034 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3([CH2:13][CH2:12][CH2:11][CH2:10]3)[O:8][B:7]([OH:14])[C:6]=2[CH:15]=1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3([CH2:13][CH2:12][CH2:11][CH2:10]3)[O:8][B:7]([OH:14])[C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866854776-methyl-1H-spiro[2,1-benzoxaborole-3,1'-cyclopentane]-1-ol

Product 1

HCID 866854796-(bromomethyl)-1H-spiro[benzo[c][1,2]oxaborole-3,1'-cyclopentan]-1-olYield 71.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 6-methyl-1H-spiro[benzo[c][1,2]oxaborole-3,1′-cyclopentan]-1-ol (1.2 g, 6.0 mmol) in CCl4 (10 mL) under nitrogen was added NBS (1.07 g, 6.0 mmol) and BPO (145 mg, 0.6 mmol). The mixture was heated at reflux 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 on column chromatography to provide the product (1.2 g, yield 71.7%).

Workup

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

Sources & evidence

ORD record
ord-739ee89264ae4244a0dbbb0dbc5868c8
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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