Azobisisobutyronitrile → 2-[2-(Bromomethyl)-6-methylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 634071Notes

Reaction equation

HRID 634071 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[B:9]1[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]1.[Br:18]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(#N)C>[Br:18][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[B:9]1[O:10][C:11]([CH3:17])([CH3:16])[C:12]([CH3:15])([CH3:14])[O:13]1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 104897161,3,2-Dioxaborolane, 2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-

Product 1

HCID 1317354802-[2-(Bromomethyl)-6-methylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 43.0 g (185 mmol) of 2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 42.9 g (241 mmol) of N-bromosuccinimide, and 0.40 g (3.27 mmol) of AIBN in 1000 ml of acetonitrile was refluxed for 2 h. Then, this mixture was cooled to room temperature and evaporated to dryness. The residue was dissolved in 500 ml of hexane. The precipitate was filtered on glass frit (G3), and the filtrate was evaporated to dryness to give yellowish crystalline solid. Yield 37.9 g (66%). Anal. calc. for C14H20BBrO2: C, 54.06; H, 6.48. Found: C, 54.35; H, 6.72. 1H NMR (CDCl3): δ 7.21 (m, 1H, 4-H), 7.15 (m, 1H, 3-H), 7.07 (m, 1H, 5-H), 4.72 (s, 2H, CH2Br), 2.44 (s, 3H, 6-Me), 1.42 (s, 12H, Bpin).

Workup

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

Sources & evidence

ORD record
ord-93d28b1f9817485a9213aca384db5daa
Source dataset
uspto-grants-2016_04
Patent number
US09321858B2

Reaction notes

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