1-Chloro-4-iodobenzene → HCID 67975703, compound

HRID 1844089Notes

Reaction equation

HRID 1844089 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH:3]2[CH2:7][CH:8]3[C:13]([CH:12]=[CH:11][CH:10]=[CH:9]3)=[C:2]12.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.[Cu-]=O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:1]2[C:5](=[O:6])[CH2:4][CH:3]3[CH2:7][C:8]4[C:13]([CH:2]23)=[CH:12][CH:11]=[CH:10][CH:9]=4)=[CH:17][CH:16]=1

Participants

8

Reactant 3

HCID 125101-Chloro-4-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 67975699HCID 67975699, compound

Product 1

HCID 67975703HCID 67975703, compound

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of tetrahydro-1H-indeno[1,2-b]pyrrol-2-one (1.00 g, 5.77 mmol) in water (3 mL) was added copper (I) oxide (167 mg), p-chloroiodobenzene (1.38 g, 5.77 mmol), tetrabutylammonium bromide (0.372 g, 1.15 mmol) and potassium phosphate (2.45 g, 11.5 mmol). The suspension was vigorously stirred at 130° C. overnight. The mixture was cooled down and diluted with dichloromethane. The solid were filtered off and the organic layer was dried and concentrated. The residue was purified by flash chromatography with a gradient of ethyl acetate in cyclohexane of 1 to 60%, to give the desired product F16 (600 mg, 39%). LCMS (method A) 1.72 min; ES+: 284 (M+H+).

Workup

  1. temperatureThe mixture was cooled down
  2. filtrationThe solid were filtered off
  3. customthe organic layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography with a gradient of ethyl acetate in cyclohexane of 1 to 60%

Sources & evidence

ORD record
ord-d587816812ba420cb378ede02f8a045d
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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