Water → HCID 11346467, compound

HRID 1169282Notes

Reaction equation

HRID 1169282 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.[CH:13]1(Br)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>CN(C=O)C.C1C=CC=CC=1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:11]#[N:12])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7960Cyclohexyl bromideHCID 24758Sodium hydrideHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 11346467HCID 11346467, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of NaH (1.1 g, 27.5 mmol) in DMF (15 mL) and benzene (30 mL) at 0° C. was treated dropwise with 4-bromophenylacetonitrile (5.0 g, 25.5 mmol), stirred for 45 minutes, treated portionwise with cyclohexyl bromide (3.15 mL, 25.5 mmol), warmed to room temperature, stirred for 90 minutes, treated with water, and extracted with diethyl ether. The extract was washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5:1 hexanes/ethyl acetate to provide the desired product.

Workup

  1. stirringstirred for 90 minutes
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 5:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-ec2d5fc2043c4431a69859d68fbaf890
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

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