Potassium Carbonate → HCID 71062820, compound

HRID 576580Notes

Reaction equation

HRID 576580 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]([CH3:13])[CH3:12].I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>[Cu]Br.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:6]=[C:5]2[CH:11]([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 14798Sodium HydroxideHCID 12137096HCID 12137096, compound

Product 1

HCID 71062820HCID 71062820, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 24593copper(I) bromideCatalyst

Conditions

Temperature
100 °C

Procedure

Copper(I) bromide (66 mg, 0.462 mmol) was added to a solution of 94A (1.1 g, 4.62 mmol) in iodo benzene (3.77 g, 18.48 mmol) followed by potassium carbonate (2.55 g, 18.48 mmol), and the mixture was stirred at 100° C. for 10 min. NaOH (150 mg, 3.75 mmol) and copper(II) acetate (10 mg, 0.055 mmol) was added at 140° C., and the mixture was stirred for 9 h. Insoluble solids were filtered, the filtrate was concentrated and partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography using 8% ethyl acetate in hexane to afford title compound (1.0 g, 68.9%) as an oil. 1H NMR (300 MHz, CDCl3): δ 7.80 (d, J=2.1 Hz, 1H), 7.54-7.42 (m, 5H), 7.4-7.28 (m, 2H), 7.21-7.08 (m, 2H), 3.19 (m, 1H), 1.38 (d, J=6.9 Hz, 6H).

Workup

  1. stirringthe mixture was stirred for 9 h
  2. filtrationInsoluble solids were filtered
  3. concentrationthe filtrate was concentrated
  4. custompartitioned between ethyl acetate and water
  5. customOrganic layer was separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. custompurified by flash chromatography

Sources & evidence

ORD record
ord-55a9e37e67bf49ad96e9547f7f4c06c5
Source dataset
uspto-grants-2015_05
Patent number
US09040517B2

Reaction notes

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