1,3-Diiodopropane → 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutanecarbonitrile

HRID 1853909

Reaction equation

HRID 1853909 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=2)[O:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].I[CH2:30][CH2:31][CH2:32]I>C1COCC1>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:18])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:16]#[N:17])[CH2:32][CH2:31][CH2:30]3)=[CH:11][CH:10]=2)[O:5]1

Participants

5

Reactant 3

HCID 123141,3-DiiodopropaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 38429222-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile

Product 1

HCID 580346631-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutanecarbonitrileYield 48.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (7.0 g, 29 mmol) in THF at 0° C. was added NaHMDS (1.0 M, 120 mL, 120 mmol). After stirring for 20 min 1,3-diiodopropane (26 g, 86 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was cooled to 0° C., quenched with MeOH (5.0 mL) and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (4.0 g, 47%) as a yellow oil: ESI MS m/z 286 [C17H22BNO2+H]+.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched with MeOH (5.0 mL)
  4. customthe residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-50a100c791c649b49232818f576ab13a
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Linked notes

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