4-Toluenesulfonyl chloride → HCID 86586227, compound

HRID 1370836Notes

Reaction equation

HRID 1370836 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Br:12][C:13]1[CH:19]=[CH:18][C:16]([OH:17])=[CH:15][C:14]=1[OH:20].C([O-])([O-])=O.[K+].[K+].[CH2:27](Br)[CH:28]=[CH2:29]>CC(C)=O>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:17][C:16]2[CH:18]=[CH:19][C:13]([Br:12])=[C:14]([O:20][CH2:29][CH:28]=[CH2:27])[CH:15]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 811054-Bromoresorcinol

Product 1

HCID 86586227HCID 86586227, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

p-Toluenesulfonylchloride (2.14 g, 11.2 mmoles) was added to a solution of 4-bromoresorcinol (2.12 g, 11.2 mmoles) and K2CO3 (10.0 g, 72.4 mmoles) in acetone (150 mL). The reaction was heated to 60° C. overnight, treated with allyl bromide (2.6 mL, 30.3 mmoles), and heated to 60° C. for 24 h (according to Bos, M. E.; Wulff, W. D.; Miller, R. A.; Chamberlin, S.; Brandvoid, T. A. J. Am. Chem. Soc. 1991, 113, 9293). The reaction was cooled to room temperature, quenched with aqueous NH4Cl, and concentrated under reduced pressure. The crude products were diluted with diethyl ether, extracted with H2O, washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography on a prepacked Biotage colum (hexane to 4:1 hexane:ethyl acetate) on silica gel to provide the title compound (3.50 g, 81%) as a clear colorless oil.

Workup

  1. temperatureheated to 60° C. for 24 h (
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with aqueous NH4Cl
  4. concentrationconcentrated under reduced pressure
  5. additionThe crude products were diluted with diethyl ether
  6. extractionextracted with H2O
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography on a prepacked Biotage colum (hexane to 4:1 hexane:ethyl acetate) on silica gel

Sources & evidence

ORD record
ord-78630ef780144085ab3341d31c038f6d
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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