Dimethylformamide → 4-(1-Hydroxy-2-methylbutyl)benzonitrile

HRID 911657Notes

Reaction equation

HRID 911657 reaction equation
[OH:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)[CH:3]([CH3:6])[CH2:4][CH3:5].[CH3:14][N:15](C=O)C>O.[C-]#N.[Zn+2].[C-]#N>[OH:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([C:14]#[N:15])=[CH:9][CH:8]=1)[CH:3]([CH3:6])[CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 108477881-(4-Bromophenyl)-2-methylbutan-1-ol

Product 1

HCID 576562264-(1-Hydroxy-2-methylbutyl)benzonitrileYield 75%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Add 4-(1-hydroxy-2-methyl-butyl)-1-bromo-benzene (1.9 g, 7.8 mmol), zinc cyanide (1.82 g, 15.6 mmol), and tetrakistriphenylphosphine palladium(0) (260 mg, 0.22 mmol) to anhydrous DMF (40 mL) under a nitrogen atmosphere. Heat the mixture at 90° C. for 12 h. Cool the mixture to room temperature, dilute with water and extract the aqueous phase twice with dichloromethane. Wash the combined organic extracts with water and brine. Dry the organic solution over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 20:1) to provide the desired intermediate (1.2 g, 75%). MS (APCI) m/z: 190 (M+H)+.

Workup

  1. temperatureCool the mixture to room temperature
  2. extractionextract the aqueous phase twice with dichloromethane
  3. washWash the combined organic extracts with water and brine
  4. dry with materialDry the organic solution over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 20:1)

Sources & evidence

ORD record
ord-9d1b5d30a67d41008b2fcb66b84d30de
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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