Iodosylbenzene → HCID 86685927, compound

HRID 2277597Notes

Reaction equation

HRID 2277597 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH2:8][NH:7][CH2:6][CH2:5]2.[Br-].[K+].I(C1C=CC=CC=1)=[O:16]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[C:8](=[O:16])[NH:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 92125IodosylbenzeneHCID 253877Potassium BromideHCID 84660332HCID 84660332, compound

Product 1

HCID 86685927HCID 86685927, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-chloro-7-fluoro-1,2,3,4-tetrahydro-isoquinoline (130 mg, 0.7 mmol), potassium bromide (83.5 mg, 0.7 mmol) and iodoso benzene (0.46 g, 2.1 mmol) in water (4 mL) was stirred at room temperature overnight. The mixture was then extracted with EtOAc and the organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product. Flash column chromatography separation (silica gel, 12 g, 30% EtOAc in hexane) then afforded the tile compound (58 mg, 41%) as a white solid.

Workup

  1. extractionThe mixture was then extracted with EtOAc
  2. customthe organic layer was dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated in vacuo
  5. customto give a crude product
  6. customFlash column chromatography separation (silica gel, 12 g, 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-94adea735dae40eabede89f24375ef04
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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