Succinimide → 2-[2-(Bromomethyl)-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1097183Notes

Reaction equation

HRID 1097183 reaction equation
[CH3:1][C:2]1[C:7]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]2)=[CH:6][C:5]([C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1.C1C(=O)N([Br:28])C(=O)C1.C1(=O)NC(=O)CC1>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[Br:28][CH2:1][C:2]1[C:7]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:11])([CH3:12])[O:9]2)=[CH:6][C:5]([C:17]([F:19])([F:18])[F:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 579349502-Methyl-5-trifluoroMethylphenylboronic acid, pinacol ester

Product 1

HCID 1190066772-[2-(Bromomethyl)-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 98.6%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

6-Methyl-3-(trifluoromethyl)phenylboronic acid pinacol ester (24b, 3.0 g, 10 mmol) and 60 ml CCl4 were placed in 500 ml round-bottom flask. NBS (1.9, 10.5 mmol, 1.05 eq) and AIBN (0.02 g, 0.14 mmol, 0.014 eq) were added and the reaction mixture was refluxed for 4.5 h in the presence of 75 W incandescent bulb. After 4.5 h the solution was cooled down to room temperature allowing the succinimide to precipitate out. The solid was filtered off. The solvent was removed and oily product was collected. The crude product was purified by triturating with hexane which resulted in 80% pure product (25b, 3.6 g, 95% yield).

Workup

  1. temperaturethe reaction mixture was refluxed for 4.5 h in the presence of 75 W incandescent bulb
  2. customto precipitate out
  3. filtrationThe solid was filtered off
  4. customThe solvent was removed
  5. customoily product was collected
  6. customThe crude product was purified
  7. customby triturating with hexane which

Sources & evidence

ORD record
ord-dad7e33e47204cc39112b29d0e1b721f
Source dataset
uspto-grants-2012_03
Patent number
US08143068B2

Reaction notes

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