o-Xylyl bromide → HCID 65376405, compound

HRID 1621010Notes

Reaction equation

HRID 1621010 reaction equation
[Li]CCCC.C(NC(C)C)(C)C.[CH:13]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14]1.Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27]>C1COCC1>[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:13]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 6992o-Xylyl bromideHCID 7912DiisopropylamineHCID 78148CyanocyclobutaneHCID 178418339Butyllithium

Product 1

HCID 65376405HCID 65376405, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-BuLi (0.018 mol, 7.2 ml, 2.5M) was added to a solution of diisopropylamine (1.7 g, 0.017 mol) in THF (15 mL) at −78° C. After 5 minutes neat cyclobutancarbonitrile (1.2 g, 0.015 mol) was added and the mixture was stirred at −78° C. for 1 hour. Then a solution of 1-(bromomethyl)-2-methylbenzene (3.3 g, 0.018 mol) in THF (3 mL) was added and the mixture was stirred at −78° C. for 1 hour. The mixture was quenched with water and extracted with EtOAc. The organic phase was concentrated and the residue was directly used to the next step without further purification. MS: m/z 186 (M+H)

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 hour
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. concentrationThe organic phase was concentrated
  5. customthe residue was directly used to the next step without further purification

Sources & evidence

ORD record
ord-355a28d43c764865a3d20737b93a581f
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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