Water → HCID 67148437, compound

HRID 2428164Notes

Reaction equation

HRID 2428164 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[NH:9]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.O>CN(CCO)C.[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:9]2[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 115221-Bromo-4-iodobenzeneHCID 2733874(3S)-pyrrolidin-3-olHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 67148437HCID 67148437, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 79022-(Dimethylamino)ethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 1-bromo-4-iodo-benzene (50.0 g, 177 mmol), (S)-pyrrolidin-3-ol (28.6 mL, 353 mmol), CuI (6.73 g, 35.3 mmol) and K3PO4.H2O (81.4 g, 353 mmol) in N,N-dimethylaminoethanol (177 mL) was stirred at 55° C. for 60 h. The mixture was allowed to cool to rt, and water was added. The mixture was extracted several times with CH2Cl2. The combined org. extracts were washed with a 1:1 mixture of aq. conc. NH3 and water. The NH3-containing aq. layer was extracted with CH2Cl2. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization of the crude from EtOAc/heptane yielded the title compound (36.1 g, 84%).

Workup

  1. temperatureto cool to rt
  2. extractionThe mixture was extracted several times with CH2Cl2
  3. washextracts were washed with a 1:1 mixture of aq. conc. NH3 and water
  4. additionThe NH3-containing aq. layer
  5. extractionwas extracted with CH2Cl2
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customCrystallization of the crude from EtOAc/heptane

Sources & evidence

ORD record
ord-faaf1c244e6943e08862af7f82e1e3ed
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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