4-tert-Butylphenol → HCID 58555139, compound

HRID 918939Notes

Reaction equation

HRID 918939 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:13]1[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:39][C:40]1[CH:41]=[C:42]([OH:47])[CH:43]=[C:44]([CH3:46])[CH:45]=1>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:13]2[CH:18]=[CH:17][C:16]([O:47][C:42]3[CH:43]=[C:44]([CH3:46])[CH:45]=[C:40]([CH3:39])[CH:41]=3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 73934-tert-ButylphenolHCID 79483,5-DimethylphenolHCID 10796Cesium carbonateHCID 125101-Chloro-4-iodobenzeneHCID 707002,2,6,6-Tetramethyl-3,5-heptanedione

Product 1

HCID 58555139HCID 58555139, compoundYield 80%

Conditions

Temperature
140 °C

Procedure

Following the general procedure (135° C., 24 hours), 4-tert-butylphenol (1.5 mmol) was coupled with 4-chloroiodobenzene (1.5 mmol). Then 0.1 eq. CuBr, 0.8 eq. Ligand 2,2,6,6-tetramethyl-3,5-heptanedione, 2.5 eq, Cs2CO3 and 1.5 mmol 3,5-dimethylphenol were added under N2, and reaction was sealed and heated at 140° C. for 36 hours. The crude brown oil was purified by flash chromatography on silica gel (eluent: cyclohexane) to provide 80% yield of the desired product as an oil.

Workup

  1. customreaction
  2. customwas sealed
  3. customThe crude brown oil was purified by flash chromatography on silica gel (eluent: cyclohexane)

Sources & evidence

ORD record
ord-615e7395788241ee90c6153cbf37301e
Source dataset
uspto-grants-2016_03
Patent number
US09272274B2

Reaction notes

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