Dimethylformamide → HCID 68671759, compound

HRID 2071042Notes

Reaction equation

HRID 2071042 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[C:4]([Br:13])[CH:3]=1.[NH4+].[OH-].[CH3:16][N:17](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:13][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=1)[C:16]#[N:17]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 17908432HCID 17908432, compound

Product 1

HCID 68671759HCID 68671759, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 1.37 g (4.17 mmol) of 1,3-dibromo-5-(methylsulfonylmethyl)benzene, 297 mg (2.53 mmol) of Zn(CN)2, and 298 mg (0.258 mmol) of Pd(PPh3)4 in 10 mL of DMF (degassed) was heated at 80° C. After 2.5 h, a 10% NH4OH aqueous solution was added, and the aqueous layer was extracted with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (50-60) % EtOAc/hexanes provided 228 mg of 3-bromo-5-(methylsulfonylmethyl)benzonitrile as a colorless solid in 20% yield.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (50-60) % EtOAc/hexanes

Sources & evidence

ORD record
ord-42c3739ce6464fcd80050e2e1e78bb15
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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