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Sodium Iodide → 1-[3-(1-Iodomethyl-cyclobutyl)-prop-1-ynyl]-4-trifluoromethoxy-benzene

HRID 852417
Notes
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Reaction equation

HRID 852417 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH2:12][C:13]2([CH2:17]OS(C)(=O)=O)[CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1.[Na+].[I-:26]>CC(=O)CC>[I:26][CH2:17][C:13]1([CH2:12][C:11]#[C:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:24])([F:23])[F:1])=[CH:5][CH:6]=2)[CH2:16][CH2:15][CH2:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86602545Methanesulfonic acid 1-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-cyclobutylmethyl ester

Product 1

HCID 694591641-[3-(1-Iodomethyl-cyclobutyl)-prop-1-ynyl]-4-trifluoromethoxy-benzeneYield 87.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 0.78 g (2.15 mmol) methanesulfonic acid 1-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-cyclobutylmethyl ester in 30 ml 2-butanone was added 0.65 g (4.30 mmol) NaI. The mixture was heated for 9 h at 90° C. The solvent was evaporated and the residue suspended in dichloromethane, ether was added and the suspension was filtrated. Evaporation of the organic phase gave 0.74 g of the title compound as dark brown oil.

Workup

  1. customThe solvent was evaporated
  2. additionether was added
  3. filtrationthe suspension was filtrated
  4. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-f07aa00aa59e491c9e41fb1e3b0bded0
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253192B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes