1,3-Propanediol → 2-(1,3,2-Dioxaborinan-2-yl)benzonitrile

HRID 2363765Notes

Reaction equation

HRID 2363765 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[B:9]([OH:11])[OH:10])#[N:2].[CH2:12](O)[CH2:13][CH2:14]O>C(Cl)Cl>[O:10]1[CH2:14][CH2:13][CH2:12][O:11][B:9]1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 104421,3-PropanediolHCID 27346102-Cyanophenylboronic acid

Product 1

HCID 35296022-(1,3,2-Dioxaborinan-2-yl)benzonitrileYield 57.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

49.0 g (334 mmol) 2-cyanobenzeneboronic acid and 25.9 g (340 mmol) 1,3-propanediol were dissolved in 1 L CH2Cl2 with stirring in a 2 L round bottom flask for 20 h. The solution was then poured over a filter with suction to remove gummy solids. The filtrate was then dried with anhydrous MgSO4 to remove residual water, filtered and evaporated of solvent to give light-colored oil. The oil was then dissolved in CH2Cl2 and purified on a silica gel plug using CH2Cl2 as eluent. The product fractions were evaporated down to give the product as clear oil (35.7 g, 57.2% yield).

Workup

  1. additionThe solution was then poured over
  2. filtrationa filter with suction
  3. customto remove gummy solids
  4. dry with materialThe filtrate was then dried with anhydrous MgSO4
  5. customto remove residual water
  6. filtrationfiltered
  7. customevaporated of solvent
  8. customto give light-colored oil
  9. custompurified on a silica gel plug
  10. customThe product fractions were evaporated down

Sources & evidence

ORD record
ord-f3e3642a6f6747b5846d373cf2a2dce5
Source dataset
uspto-grants-2014_04
Patent number
US08691988B2

Reaction notes

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