1,5-Dibromopentane → HCID 15030111, compound

HRID 1072004Notes

Reaction equation

HRID 1072004 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:10]#[N:11])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 15030111HCID 15030111, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

(3-Methoxyphenyl)acetonitrile (0.52 grams) was added to a solution of sodium hydride (0.212 grams) in DMSO (10 mL) at 0° C. The mixture was warmed to room temperature over 30 minutes. 1,5-Dibromopentane (0.722 mL) was added dropwise as a solution in DMSO (5 mL). This mixture was stirred for 16 hours, then partitioned between ethyl acetate and water. The organic phase was separated and washed with brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated. The resulting solid was chromatographed on silica gel using ethyl acetate and hexane (3:97) to give the titled compound (0.42 grams).

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe resulting solid was chromatographed on silica gel

Sources & evidence

ORD record
ord-2857e5b0f5f64bc18e424f5e1f4483fc
Source dataset
uspto-grants-2005_06
Patent number
US06908934B2

Reaction notes

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