Nitrogen → HCID 69079990, compound

HRID 1822322Notes

Reaction equation

HRID 1822322 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1.Br[C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21](Br)[CH:22]=1.[C:25](=[O:28])([O-])[O-:26].[Cs+].[Cs+].C[C:32]([CH3:43])([C:34](=O)[CH2:35][C:36](=[O:41])[C:37]([CH3:40])(C)C)C.N#N.CN1C[CH2:50][CH2:49][C:48]1=O>[Cu]Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[CH:22]=[C:21]([CH:20]=[C:19]([CH3:24])[CH:18]=2)[O:41][C:36]2[CH:37]=[CH:40][C:48]([CH2:49][CH2:50][C:25]([OH:26])=[O:28])=[C:34]([CH2:32][CH3:43])[CH:35]=2)=[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1

Participants

8

Reactant 6

HCID 947NitrogenHCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 153613,5-DibromotolueneHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 127742954-Chloro-2-phenoxyphenol

Product 1

HCID 69079990HCID 69079990, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 4-chloro-2-phenoxy-phenol (6.46 g, 29.3 mmol), 3,5-dibromotoluene (21.95 g, 87.8 mmol), cesium carbonate (11.45 g, 35.1 mmol), and 2,2,6,6-tetramethyl-3,5-heptanedione (1.35 g, 7.33 mmol) in 1-methyl-2-pyrrolidinone (65 mL) is purged with N2, and copper (I) chloride (1.45 g, 14.6 mmol) is added. The reaction heated to 120° C. for 20 hours under N2. The reaction is cooled and quenched with 1 N HCl (20 mL). The mixture is then diluted with water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 100% hexanes to afford 7.84 g (69%) of the title compound. Rf=0.49 (9/1 hexanes/ethyl acetate). 1H NMR (400 MHz, CDCl3).

Workup

  1. additionis added
  2. temperatureThe reaction is cooled
  3. customquenched with 1 N HCl (20 mL)
  4. additionThe mixture is then diluted with water
  5. extractionextracted with Et2O
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. customthe solvent is removed in vacuo
  8. customto afford crude product that
  9. customis absorbed on silica gel
  10. custompurified by flash chromatography

Sources & evidence

ORD record
ord-aad5e9ddcabe462485fb1a3f71ecf3bb
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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