Azobisisobutyronitrile → 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Bromide

HRID 634067Notes

Reaction equation

HRID 634067 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[O:3]1.[Br:17]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(#N)C>[Br:17][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[B:4]1[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 107040082-Tolylboronic acid pinacol ester

Product 1

HCID 38348342-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 32.3 g (148 mmol) of 4,4,5,5-tetramethyl-2-(2-methylphenyl)-1,3,2-dioxaborolane, 25.0 g (141 mmol) of N-bromosuccinimide, and 0.32 g (2.62 mmol) of AIBN was refluxed in 1000 ml of acetonitrile for 2 h. The mixture was then cooled to room temperature and then evaporated to dryness. The residue was dissolved in 500 ml of hexane. The formed precipitate was filtered on glass frit (G3), and the filtrate was evaporated to dryness to give yellowish crystalline powder. Yield 28.9 g (66%). Anal. calc. for C13H18BBrO2: C, 52.57; H, 6.11. Found: C, 52.63; H, 6.29. 1H NMR (CDCl3): 7.81 (m, 1H, 6-H), 7.37-7.42 (m, 2H, 3, 5-H), 7.28 (m, 1H, 4-H), 4.91 (s, 2H, CH2Br), 1.37 (s, 1H, Bpin).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in 500 ml of hexane
  3. filtrationThe formed precipitate was filtered on glass frit (G3)
  4. customthe filtrate was evaporated to dryness
  5. customto give yellowish crystalline powder

Sources & evidence

ORD record
ord-cf7efa7c98254b8b8680a420051a27f3
Source dataset
uspto-grants-2016_04
Patent number
US09321858B2

Reaction notes

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