Hydrochloric Acid → 4-(3-Iodopropyl)benzonitrile

HRID 1071966Notes

Reaction equation

HRID 1071966 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.CCN(CC)CC.CS(Cl)(=O)=O.Cl.[Na+].[I-:27]>C(Cl)Cl>[I:27][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 110841784-(3-Hydroxypropyl)benzonitrile

Product 1

HCID 223906924-(3-Iodopropyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-hydroxypropyl)benzonitrile (1.8 g, 11.2 mmol) in CH2Cl2 (50 mL) at 0° C., Et3N (1.06 mL, 13.4 mmol) and then MsCl (0.95 mL, 12.5 mmol) were added. Upon completion, the reaction mixture was poured into 0.5M HCl and extracted with EtOAc. The crude mesylate was dissolved in acetone and treated with NaI (3.0 g, 20.0 mmol) in the dark at room temperature. When complete, the reaction was purified by flash chromatography on silica gel eluting with 15% EtOAc in Hexanes to afford the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dissolutionThe crude mesylate was dissolved in acetone
  3. customWhen complete, the reaction was purified by flash chromatography on silica gel eluting with 15% EtOAc in Hexanes

Sources & evidence

ORD record
ord-1274748071144e62950bc8a19cf6a41b
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

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